Ethyl 3-isothiocyanatobutanoate → Ethyl 3-{3[(3-amino-5-chlorothien-2-yl)sulfonyl]thioureido}butanoate

HRID 1975922Notes

Reaction equation

HRID 1975922 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[C:6]([Cl:8])[S:5][C:4]=1[S:9]([NH2:12])(=[O:11])=[O:10].[N:13]([CH:16]([CH3:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:14]=[S:15]>>[NH2:2][C:3]1[CH:7]=[C:6]([Cl:8])[S:5][C:4]=1[S:9]([NH:12][C:14](=[S:15])[NH:13][CH:16]([CH3:23])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])(=[O:10])=[O:11]

Participants

3

Reactant 2

HCID 559293Ethyl 3-isothiocyanatobutanoateHCID 688206263-Amino-5-chlorothiophene-2-sulfonamide hydrochloride

Product 1

HCID 21999980Ethyl 3-{3[(3-amino-5-chlorothien-2-yl)sulfonyl]thioureido}butanoate

Procedure

The title compound was prepared from 3-amino-5-chlorothiophene-2-sulfonamide hydrochloride and ethyl 3-isothiocyanatobutyrate by a procedure analogous to the procedure described in example 3-a (yield 93%); 1H-NMR (DMSO-d6): δ1.18 (d, 3H, CH3), 1.20 (t, 3H, CH3), 2.61 (m, 2H, CH2), 4.08 (q, 2H, CH2), 4.58 (m, 1H, CH), 6.46 (br s, 2H, NH2), 6.65 (s, 1H, H-4), 8.34 (br d, 1H, NH), 11.35 (br s, 1H).

Sources & evidence

ORD record
ord-b2b606d6c73047eba11dea4761cf010f
Source dataset
uspto-grants-2001_05
Patent number
US06225310B1

Reaction notes

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