Chlorosulfonic acid → 3-Methyl-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride

HRID 1696167Notes

Reaction equation

HRID 1696167 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[CH3:12])=[O:4].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[CH3:12][C:7]1[CH:8]=[C:9]([S:16]([Cl:15])(=[O:18])=[O:17])[CH:10]=[CH:11][C:6]=1[NH:5][C:3](=[O:4])[C:2]([F:13])([F:14])[F:1]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 137696Acetamide, 2,2,2-trifluoro-N-(2-methylphenyl)-

Product 1

HCID 536276703-Methyl-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chlorideYield 85%

Conditions

Temperature
155 °C

Procedure

Synthesized according to general procedure 69. A mixture of 2,2,2-trifluoro-N-o-tolylacetamide (6.3 gm, 31 mmol) and chlorosulfonic acid (10.3 mL, 155 mmol) was heated at 155° C. for 15 min. After cooling to RT, the mixture was poured into ice water and extracted with EtOAc. The organic layer was concentrated and purified via silica gel chromatography using 0-25% EtOAc in hexanes gave 3-methyl-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (7.8 g, 85%). 1H NMR (400 MHz, DMSO-d6) δ 11.01 (s, 1H), 7.53 (d, J=1.3 Hz, 1H), 7.46 (dd, J=8.1, 1.8 Hz, 1H), 7.21 (dd, J=8.1, 2.9 Hz, 1H), 2.18 (s, 3H).

Workup

  1. customSynthesized
  2. temperatureAfter cooling to RT
  3. extractionextracted with EtOAc
  4. concentrationThe organic layer was concentrated
  5. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-72ab392def134a3595ad4492d9d2c583
Source dataset
uspto-grants-2012_04
Patent number
US08163720B2

Reaction notes

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