tert-Butyl isothiocyanate → HCID 178448904, compound

HRID 1066132Notes

Reaction equation

HRID 1066132 reaction equation
NC1C=C(Cl)C=CC=1S(N)(=O)=O.C(N=C=S)(C)(C)C.[NH2:20][C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[S:28]([NH:31][C:32]([NH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=S)(=[O:30])=[O:29]>>[C:35]([NH:34][C:32]1[NH:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=2[S:28](=[O:30])(=[O:29])[N:31]=1)([CH3:38])([CH3:37])[CH3:36]

Participants

4

Reactant 3

HCID 11544tert-Butyl isothiocyanateHCID 777902-Amino-4-chlorobenzenesulphonamideHCID 21197848HCID 21197848, compound

Product 1

HCID 178448904HCID 178448904, compound

Conditions

Temperature
60 °C

Procedure

The title compound was prepared from 2-amino-4-chlorobenzenesulfonamide and tert-butyl isothiocyanate by a method analogous to the one described in Example 4 except that the mixture was heated at 60° C. for 6 days. The intermediate N-(2-amino-4-chlorobenzenesulfonyl)-N′-tert-butylthiourea and the ring closed product were both purified by column chromatography; m.p. 291-294° C. (light petroleum/ethyl acetate); 1H-NMR (DMSO-d6): δ 1.39 (s, 9H, C(CH3)3), 6.92 (br s, 1H, NH), 7.17 (d, 1H, ArH), 7.28 (dd, 1H, ArH), 7.68 (d, 1H, ArH), 10.25 (br.s, 1H, NH); MS: m/e 287/289 (M+).

Workup

  1. customboth purified by column chromatography

Sources & evidence

ORD record
ord-b6e9fdd05d5b48b1ac14b4d9956fd176
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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