2-Amino-4-chlorobenzenesulphonamide → HCID 178527187, compound

HRID 1066128Notes

Reaction equation

HRID 1066128 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH:13]1([CH2:19][N:20]=[C:21]=S)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(OCC)(=O)C>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[S:9](=[O:11])(=[O:10])[N:12]=[C:21]([NH:20][CH2:19][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 777902-Amino-4-chlorobenzenesulphonamideHCID 142928(Isothiocyanatomethyl)Cyclohexane

Product 1

HCID 178527187HCID 178527187, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino-4-chlorobenzenesulfonamide (2.1 g, 10.16 mmol) and cyclohexylmethyl isothiocyanate (6.31 g, 40.6 mmol) was heated at 150° C. for 4 h. The mixture was allowed to cool and then stirred with 25 ml of ethyl acetate for 1 h. The precipitate was isolated by filtration and recrystallised from ethanol to give 867 mg (26%) of the title compound; m.p. 317-323° C.; 1H-NMR (DMSO-d6): δ 0.8-1.8 (m, 11H, cyclohexyl), 3.08 (t, 2H, CH2), 7.78 (m, 3H, ArH+NH), 7.68 (d, 1H, ArH), 10.52 (br.s, 1H, NH); MS: m/e 327/329 (M+); (C14H18N3Cl1O2S1) calc. C, 51.29; H, 5.53; N, 12.82; found C, 51.21; H, 5.72; N, 12.81.

Workup

  1. temperatureto cool
  2. customThe precipitate was isolated by filtration
  3. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-088eeea86a9c451f99322650bb49c96f
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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