Isopropyl Isothiocyanate → N-(3-Amino-5-chloro-2-thienylsulfonyl)-N'-isopropylthiourea

HRID 1419742Notes

Reaction equation

HRID 1419742 reaction equation
CC(C)([O-])C.[K+].Cl.[NH2:8][C:9]1[CH:13]=[C:12]([Cl:14])[S:11][C:10]=1[S:15]([NH2:18])(=[O:17])=[O:16].[CH:19]([N:22]=[C:23]=[S:24])([CH3:21])[CH3:20]>CN(C)C=O>[NH2:8][C:9]1[CH:13]=[C:12]([Cl:14])[S:11][C:10]=1[S:15]([NH:18][C:23]([NH:22][CH:19]([CH3:21])[CH3:20])=[S:24])(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 75263Isopropyl IsothiocyanateHCID 23665647Potassium tert-butoxideHCID 688206263-Amino-5-chlorothiophene-2-sulfonamide hydrochloride

Product 1

HCID 11066983N-(3-Amino-5-chloro-2-thienylsulfonyl)-N'-isopropylthioureaYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium tert-butoxide (0.49 g, 4.4 mmol) was added to a solution of 3-amino-5-chlorothiophene-2-sulfonamide hydrochloride (0.5 g, 2.0 mmol) in dry N,N-dimethylformamide (5 ml) with stirring on an ice bath. After 5 min, isopropyl isothiocyanate (0.26 ml, 2.4 mmol) was added dropwise to the resulting suspension, and the mixture was stirred for 30 min at 0° C. The cooling bath was removed, and stirring was continued at room temperature for 30 min. The solvent was evaporated at <50° C., and the residue was taken up in 25 ml of water, treated with decolorising charcoal, and filtered. Acidification of the filtrate with acetic acid to pH 3-4 and filtration afforded 0.50 g (80%) the title compound; mp 142.0°-142.5° C. decomp., 1H-NMR (DMSO-d6): δ 1.12 (d, 6H), 4.25 (m, 1H), 6.48 (br s, 2H), 6.65 (s, 1H), 8.02 (d, 1H), 11.2 (br s, 1H).

Workup

  1. stirringthe mixture was stirred for 30 min at 0° C
  2. customThe cooling bath was removed
  3. stirringstirring
  4. waitwas continued at room temperature for 30 min
  5. customThe solvent was evaporated at <50° C.
  6. additiontreated with decolorising charcoal
  7. filtrationfiltered
  8. filtrationAcidification of the filtrate with acetic acid to pH 3-4 and filtration

Sources & evidence

ORD record
ord-dfa93903c05f486b87fd1959c94ef393
Source dataset
uspto-grants-1999_03
Patent number
US05889002

Reaction notes

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