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3-Cyclohexene-1-carboxamide,1-methyl-(7CI,9CI) synthesis
- Product Name:3-Cyclohexene-1-carboxamide,1-methyl-(7CI,9CI)
- CAS Number:69352-89-2
- Molecular formula:C8H13NO
- Molecular Weight:139.19
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Yield:69352-89-2 25 g
Reaction Conditions:
with thionyl chloride in dichloromethane;N,N-dimethyl-formamide; for 3 h;Reflux;
Steps:
Formation of 1-methylcyclohex-3-ene-1-carboxamide (52b)
Formation of 1-methylcyclohex-3-ene-1-carboxamide (52b) (2434) To a solution of 1-methylcyclohex-3-ene-1-carboxylic acid, 52a, (54.0 g, 385.2 mmol) dissolved in CH2Cl2 (200 mL) was added thionyl chloride (56.2 mL, 770.4 mmol) and 1 mL of DMF. The reaction was warmed to reflux for 3 hrs, then cooled and concentrated in vacuo. The residue was redissolved in 200 mL of CH2Cl2. To the reaction was added ammonium hydroxide (148.2 mL of 13 M solution, 1.9 mol) slowly. The reaction was stirred overnight. The reaction was extracted into CH2Cl2 and water. The organic phase was concentrated in vacuo and purified via flash silica gel chromatography (EtOAc), yielding 25 g of 1-methylcyclohex-3-ene-1-carboxamide. (2435) MS/RT: 139.96 (M+H)/2.66
References:
US9345708,2016,B2 Location in patent:Page/Page column 389
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