Phosgene → HCID 178421836, compound

HRID 1066095Notes

Reaction equation

HRID 1066095 reaction equation
NC1C=C(Cl)C(C)=CC=1S(N)(=O)=O.C(N=C=S)(C)C.[NH2:20][C:21]1[CH:26]=[C:25]([Cl:27])[C:24]([CH3:28])=[CH:23][C:22]=1[S:29]([NH:32][C:33]([NH:35][CH:36]([CH3:38])[CH3:37])=S)(=[O:31])=[O:30].C(Cl)(Cl)=O>>[Cl:27][C:25]1[C:24]([CH3:28])=[CH:23][C:22]2[S:29](=[O:31])(=[O:30])[N:32]=[C:33]([NH:35][CH:36]([CH3:38])[CH3:37])[NH:20][C:21]=2[CH:26]=1

Participants

5

Reactant 4

HCID 6371PhosgeneHCID 75263Isopropyl IsothiocyanateHCID 130015482-Amino-4-chloro-5-methylbenzene-1-sulfonamideHCID 21197836HCID 21197836, compound

Product 1

HCID 178421836HCID 178421836, compound

Procedure

Starting from 2-amino-4-chloro-5-methylbenzenesulfonamide and isopropyl isothiocyanate, and following a procedure analogous to the one described in Example 4a, N-(2-amino-4-chloro-5-methylbenzenesulfonyl)-N′-isopropylthiourea was prepared; m.p. 120-122° C. Subsequent ring closure with phosgene by a procedure analogous to the one described in Example 4b gave the title compound; 1H-NMR (d6-DMSO), δ (ppm): 10.3 (br, 1H, NH), 7.68 (1H, arom.), 7.29 (1H, arom), 7.2 (br, 1H, NH), 4.0-3.8 (m, 1H, CH), 2.37 (s, 3H, CH3), 1.20 (d, 6H, CH3).

Workup

  1. customwas prepared

Sources & evidence

ORD record
ord-77abd410cc224425859b08fc98b5c546
Source dataset
uspto-grants-2001_06
Patent number
US06242443B1

Reaction notes

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