Isopropyl Isothiocyanate → HCID 178456969, compound

HRID 1066129Notes

Reaction equation

HRID 1066129 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[S:9]([NH2:12])(=[O:11])=[O:10].[CH:13]([N:16]=[C:17]=S)([CH3:15])[CH3:14]>C(OCC)(=O)C>[F:8][C:6]1[CH:5]=[CH:4][C:3]2[S:9](=[O:11])(=[O:10])[N:12]=[C:17]([NH:16][CH:13]([CH3:15])[CH3:14])[NH:1][C:2]=2[CH:7]=1

Participants

4

Reactant 2

HCID 75263Isopropyl IsothiocyanateHCID 211978072-Amino-4-fluorobenzenesulfonamide

Product 1

HCID 178456969HCID 178456969, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 2-amino-4-fluorobenzenesulfonamide (1.9 g, 10 mmol) and isopropyl isothiocyanate (6.4 ml, 60 mmol) was heated at 140° C. for 2.5 h. The mixture was cooled to room temperature and stirred with 50 ml of ethyl acetate for 20 min. The precipitate was isolated by filtration and washed with ethyl acetate to give 355 mg (14%) of the title compound; m.p. 266-269° C.; 1H-NMR (DMSO-d6): δ 1.18 (d, 6H, CH(CH3)2), 3.91 (m, 1H, CH(CH3)2), 7.00-7.13 (m, 2H, ArH), 7.16 (br.s, 1H, NH), 7.73 (dd, 1H, ArH), 10.4 (br.s, 1H, NH); MS: m/e 257 (M+, 25%); (C10H12N3F1O2S1) calc. C, 46.68; H, 4.70; N, 16.33; found C, 46.84; H, 4.88; N, 16.13.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customThe precipitate was isolated by filtration
  3. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-d22db6594ba8410e80d2b4b7b2d5dcdb
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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