Oxalyl chloride → Benzoic acid, 2-(isocyanatosulfonyl)-, ethyl ester

HRID 745888Notes

Reaction equation

HRID 745888 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11](=[O:14])(=[O:13])[NH2:12])[CH3:2].C(Cl)(=O)[C:17](Cl)=[O:18]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[S:11]([N:12]=[C:17]=[O:18])(=[O:13])=[O:14])=[O:15])[CH3:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 4652880Ethyl 2-(Aminosulfonyl)benzoate

Product 1

HCID 13386652Benzoic acid, 2-(isocyanatosulfonyl)-, ethyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

At 85° C., 68.76 g (0.3 mol) 2-sulfamylbenzoic acid ethylester are added to 57.9 g (0.45 mol) oxalylchloride and 0.4 g diazadicyclo(2,2,2,)octane in 500 ml absolute toluene. The reaction mixture is heated yet three hours to an interior temperature of 95° C., until no gas development is observed.

Sources & evidence

ORD record
ord-1de7c85a6b5747ecb71b7b71e00fb91a
Source dataset
uspto-grants-1986_07
Patent number
US04601746

Reaction notes

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