Phosgene → HCID 178456976, compound

HRID 1975926Notes

Reaction equation

C(Cl)(Cl)=O.[Cl:5][C:6]1[S:10][C:9]([NH:11]C(=O)C)=[C:8]([S:15](=[O:24])(=[O:23])[NH:16][C:17](=S)[NH:18][CH:19]([CH3:21])[CH3:20])[CH:7]=1.C(N(CC)CC)C>O1CCCC1>[Cl:5][C:6]1[S:10][C:9]2[NH:11][C:17]([NH:18][CH:19]([CH3:20])[CH3:21])=[N:16][S:15](=[O:23])(=[O:24])[C:8]=2[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Phosgene (0.416 ml, 20% in toluene) was added dropwise to a solution of N-[5-chloro-3-(isopropylthiocarbamoyl)sulfamoylthiophen-2-yl]acetamide(261 mg, 0.73 mmol) and dry triethylamine (0.209 ml, 1.5 mmol) in dry tetrahydrofuran (5 ml) with stirring at 0° C. The mixture was stirred for 1 h at 0° C., and evaporated to dryness. The residue was triturated with 10 ml of water, and the precipitate was isolated by filtration, washed with water and finally deacetylated by stirring in 2 ml of 2 N sodium hydroxide for 90 min at room temperature. The solution was acidified to pH 2 with 4 M hydrochloric acid and the precipitate was filtered off and recrystallised from ethyl acetate with decolorising charcoal affording 44 mg (21%) of the pure title compound; mp 272-274° C. (ethyl acetate); 1H-NMR (DMSO-d6): δ1.16 (d, 6H, 2×CH3), 3.85 (m, 1H NCH), 7.23 (s, 1H, H-7), 7.48 (br d, 1H, NH), 11.12 (s, 1H, NH); MS: m/e 279/281 (M+).

Workup

stirringThe mixture was stirred for 1 h at 0° C.
customevaporated to dryness
customThe residue was triturated with 10 ml of water
customthe precipitate was isolated by filtration
washwashed with water
stirringby stirring in 2 ml of 2 N sodium hydroxide for 90 min at room temperature
filtrationthe precipitate was filtered off
customrecrystallised from ethyl acetate with decolorising charcoal affording 44 mg (21%) of the pure title compound

Sources & evidence

ORD record: ord-6693b0bedf11495387d8c4757a4f41d9
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06225310B1

Reaction notes

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