Benzoic acid, 4-[(dipropylamino)sulfonyl]-, chloromethyl ester synthesis
- Product Name:Benzoic acid, 4-[(dipropylamino)sulfonyl]-, chloromethyl ester
- CAS Number:58655-50-8
- Molecular formula:C14H20ClNO4S
- Molecular Weight:333.83
29171-72-0
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Yield:-
Reaction Conditions:
with paraformaldehyde;Zinc chloride in 1,4-dioxane;
Steps:
2 Preparation of p-(Dipropylsulfamoyl)benzoyloxymethyl chloride III
EXAMPLE 2 Preparation of p-(Dipropylsulfamoyl)benzoyloxymethyl chloride III A mixture of 40 g. of p-(dipropylsulfamoyl)benzoyl chloride II, 40 g. of paraformaldehyde and 2 g. of freshly fuzed and powdered zinc chloride in 100 ml. of dry dioxane is heated with stirring at 95°-100°C. for 5 hours and allowed to cool. The mixture is extracted with ether which is decanted and washed with sodium bicarbonate solution and with saturated ammonium sulfate solution, then dried over magnesium sulfate, and evaporated. The residue is applied on a column packed with 500 g. of silica gel and the p-(dipropylsulfamoyl)benzoyloxymethyl chloride (III) recovered by elution with methylene chloride. The yield is 25 g. of a heavy oil which partially solidifies. I.R. (in nujol) shows a C=O band at 1750 cm-1. In NMR, the CH2 Cl group appears as a singlet at 4.05τ.
References:
US3931150,1976,A