Isobutyl isothiocyanate → HCID 178448905, compound

HRID 1066126Notes

Reaction equation

HRID 1066126 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].[CH2:13]([N:17]=[C:18]=S)[CH:14]([CH3:16])[CH3:15]>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:18]([NH:17][CH2:13][CH:14]([CH3:16])[CH3:15])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 68960Isobutyl isothiocyanateHCID 777902-Amino-4-chlorobenzenesulphonamide

Product 1

HCID 178448905HCID 178448905, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 2-amino-4-chlorobenzenesulfonamide (5.0 g, 24.18 mmol) and isobutyl isothiocyanate (10 ml, 83.6 mmol) was heated at 150° C. for 3 h. The mixture was allowed to cool and then stirred with 50 ml of ethyl acetate for 30 min. The precipitate was isolated by filtration and recrystallised from ethanol to give 2.9 g (42%) of the pure title compound; m.p. 298-301° C.; 1H-NMR (DMSO-d6): δ 0.91 (d, 6H, CH(CH3)2), 1.83 (m, 1H, CH(CH3)2), 3.05 (t, 2H, CH2), 7.2-7.4 (m, 3H, ArH+NH), 7.67 (d, 1H, ArH), 10.5 (br.s, 1H, NH); MS: m/e 287/289 (M+); (C11H14N3Cl1O2S1) calc. C, 45.91; H, 4.90; N, 14.60; found C, 45.90; H, 5.04; N, 14.66.

Workup

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

Sources & evidence

ORD record
ord-ee324be6274f4edaa8faeee3e26acfe8
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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