3-Isothiocyanatoheptane → N-(3-Amino-5-chloro-2-thienylsulfonyl)-N'-(1-ethylpentyl)thiourea

HRID 1975917Notes

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

Participants

Reactant 2

HCID 5452693-Isothiocyanatoheptane

HCID 688206263-Amino-5-chlorothiophene-2-sulfonamide hydrochloride

Product 1

HCID 21999994N-(3-Amino-5-chloro-2-thienylsulfonyl)-N'-(1-ethylpentyl)thioureaYield 36%

Procedure

The title compound was prepared from 3-amino-5-chlorothiophene-2-sulfonamide hydrochloride and 1-ethylpentyl isothiocyanate by a procedure analogous to the procedure described in example 3-a; a syrup was obtained (yield 36%), 1H-NMR (DMSO-d6): δ0.8 (2 q, 6H, 2×CH3), 1.2 (m, 4H), 1.5 (m, 4H), 4.20 (sextet, 1H, CH), 6.55 (br, 2H, NH2), 6.65 (s, 1H, H4), 7.85 (br d, 1H, NH), 11.3 (br s, 1H, NH).

Workup

customa syrup was obtained (yield 36%), 1H-NMR (DMSO-d6): δ0.8 (2 q, 6H, 2×CH3), 1.2 (m, 4H), 1.5 (m, 4H), 4.20 (sextet, 1H, CH), 6.55 (br, 2H, NH2), 6.65 (s, 1H, H4), 7.85 (br d, 1H, NH), 11.3 (br s, 1H, NH)

Sources & evidence

ORD record: ord-b044b6cd27de40fea552956e6767b8d7
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225310B1

Reaction notes

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