Methane → 4-Amino-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide

HRID 619053Notes

Reaction equation

HRID 619053 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([NH:25]C(=O)C)=[CH:21][CH:20]=3)(=[O:18])=[O:17])[S:13][CH:14]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[OH-].[Na+].C>Cl>[NH2:25][C:22]1[CH:23]=[CH:24][C:19]([S:16]([NH:15][C:12]2[S:13][CH:14]=[C:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[N:11]=2)(=[O:18])=[O:17])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 21845562N-{4-[4-(3-Nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide

Product 1

HCID 104071774-Amino-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamideYield 37.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

0.47 g of N-{4-[4-(3-nitro-phenyl)-thiazol-2-ylsulphamoyl]-phenyl}-acetamide was suspended in 10 ml of 6N hydrochloric acid and heated to boiling overnight. The cooled mixture was treated with 35 ml of 2N sodium hydroxide solution. After the addition of 0.4 g of active charcoal the mixture was stirred at room temperature for 30 minutes and subsequently the active charcoal was filtered off. The product separated upon neutralization with concentrated hydrochloric acid. Recrystallization from 50 ml of 40% ethanol yielded 0.16 g of 4-amino-N-[4-(3-nitro-phenyl)-thiazol-2-yl]-benzenesulfonamide as yellowish crystals.

Workup

  1. temperatureheated
  2. filtrationsubsequently the active charcoal was filtered off
  3. customThe product separated upon neutralization with concentrated hydrochloric acid
  4. customRecrystallization from 50 ml of 40% ethanol

Sources & evidence

ORD record
ord-eaf9c2605fe9486faf7aff7d5bd15277
Source dataset
uspto-grants-1999_09
Patent number
US05958910

Reaction notes

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