Acetic Acid → methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate

HRID 2270137Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:18]=[C:17]([N+:19]([O-])=O)[CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C.Cl>[Fe].O>[NH2:19][C:17]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([S:6](=[O:8])(=[O:7])[NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

50.0 g (0.158 mol) of methyl 2-(N-tert-butylsulfamoyl)-4-nitrobenzoate (prepared according to DE-OS 4 236 902) are added to a mixture of 180 ml of acetic acid and 75 ml of water, and the mixture is heated to 80° C. 26.5 g (0.474 mol) of iron powder are added a little at a time in such a manner that the temperature does not rise above 85° C. The mixture is subsequently stirred at 80° C. for 4 h, 85 ml of 2N HCl are added at this temperature and the mixture is allowed to cool to 25° C. The mixture is filtered off and the solid is washed thoroughly with water. The solid is subsequently 3× extracted hot with in each case 250 ml of ethyl acetate. The ethyl acetate phase is evaporated, and the residue is triturated with diisopropyl ether and dried. This gives 37.7 g (83% of theory) of methyl 4-amino-2-(N-tert-butylsulfamoyl)benzoate of m.p. 198-1990° C.

Workup

customdoes not rise above 85° C
temperatureto cool to 25° C
filtrationThe mixture is filtered off
washthe solid is washed thoroughly with water
extractionextracted hot with in each case 250 ml of ethyl acetate
customThe ethyl acetate phase is evaporated
customthe residue is triturated with diisopropyl ether
customdried

Sources & evidence

ORD record: ord-d29eab2e1cab4fd892e70843f06e0a1f
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06331506B1

Reaction notes

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