Chlorosulfonic acid → HCID 86758935, compound

HRID 2120373Notes

Reaction equation

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

Participants

Reactant 2

HCID 24638Chlorosulfonic acid

HCID 10709461HCID 10709461, compound

Product 1

HCID 86758935HCID 86758935, compoundYield 45.2%

Conditions

Temperature: 85 °C

Procedure

(R)-N-{2,3-Dichlorophenyl)-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Method 74) (5.0 g, 16.6 mmol) was added in portions to cooled (0° C.) chlorosulphonic acid (5.3 ml, 81 mmol) over 15 mins and then the mixture was heated to 85° C. for 4.5 hours. The reaction mixture was cooled in an ice bath and then poured slowly onto a stirred ice-water mixture (60 ml). The mixture was extracted with DCM (2×75 ml), the DCM washed with brine, dried and evaporated. The residue was chromatographed on silica with 20% EtOAc in hexane as eluent to give the title compound as a solid (3.0 g, 7.5 mmol). NMR (CDCl3): 1.8 (s, 3H), 3.4 (s, 1H), 8.15 (d, 1H), 8.65 (d, 1H) and 9.55 (brs, 1H); m/z 400.

Workup

temperatureThe reaction mixture was cooled in an ice bath
extractionThe mixture was extracted with DCM (2×75 ml)
washthe DCM washed with brine
customdried
customevaporated
customThe residue was chromatographed on silica with 20% EtOAc in hexane as eluent

Sources & evidence

ORD record: ord-c730cfe80e104b128abaae7501ee0ecb
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689909B1

Reaction notes

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