Isoamyl isothiocyanate → HCID 10991483, compound

HRID 1975915Notes

Reaction equation

HRID 1975915 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].[CH3:19][CH:20]([CH3:26])[CH2:21][CH2:22][N:23]=[C:24]=[S:25]>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:24]([NH:23][CH2:22][CH2:21][CH:20]([CH3:26])[CH3:19])=[S:25])(=[O:16])=[O:17]

Participants

5

Reactant 3

HCID 79086Isoamyl isothiocyanateHCID 23665647Potassium tert-butoxideHCID 688206263-Amino-5-chlorothiophene-2-sulfonamide hydrochloride

Product 1

HCID 10991483HCID 10991483, compoundYield 30.7%

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 10 min, 3-methylbutyl isothiocyanate (0.31 g, 2.4 mmol) was added dropwise to the resulting suspension, and the mixture was stirred for 3.5 h at 0 to 20° C. Most of the solvent was evaporated at 40° C., and the residue was taken up in 25 ml of water, treated with decolourising charcoal, and filtered. Acidification of the filtrate with acetic acid to pH 3-4 and filtration afforded 0.21 g (29%) of the title compound; mp 114-115° C. decomp., 1H-NMR (DMSO-d6): δ0.85 (d, 6H, 2×CH3), 1.40 (q, 2H, CH2), 1.50 (m, 1H, CH), 3.45 (q, 2H, CH2), 6.45 (br, 2H, NH2), 6.65 (s, 1H, H4), 8.30 (br t, 1H, NH), 11.3 (br s, 1H).

Workup

  1. stirringthe mixture was stirred for 3.5 h at 0 to 20° C
  2. customMost of the solvent was evaporated at 40° C.
  3. additiontreated with decolourising charcoal
  4. filtrationfiltered
  5. filtrationAcidification of the filtrate with acetic acid to pH 3-4 and filtration

Sources & evidence

ORD record
ord-b889f3a7d949473f9e5cc668008978e3
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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