Hydrochloric Acid → 4-amino-N-benzyl-3-nitrobenzene-1-sulfonamide

HRID 2064689Notes

Reaction equation

C(OC(=O)[NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:22])(=[O:21])[NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24])C.[OH-].[Na+].Cl>C(O)C>[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:22])=[O:21])=[CH:8][C:7]=1[N+:23]([O-:25])=[O:24]

Participants

Conditions

Temperature: 75 °C

Procedure

To a stirred suspension of (4-Benzylsulfamoyl-2-nitro-phenyl)-carbamic acid ethyl ester (1.50 g, Reference Example 62) in ethanol (30 ml) was added 2M sodium hydroxide solution (5.93 ml) and the reaction heated at 75° C. for 2 hours. The reaction mixture was cooled to ambient temperature, poured onto ice-water and acidified to pH3 with 2M hydrochloric acid (30 ml). The resultant precipitate was collected by filtration and dried in vacuo to give 4-amino-N-benzyl-3-nitro-benzenesulfonamide (1.01 g) as a yellow solid. LC-MS (METHOD J): RT=3.41 minutes, 308.22 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
additionpoured onto ice-water
filtrationThe resultant precipitate was collected by filtration
customdried in vacuo

Sources & evidence

ORD record: ord-7b5c0c37f2834f88a897e1c8c58e749a
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08288425B2

Reaction notes

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