Chlorosulfonic acid → HCID 53761610, compound

HRID 1603238Notes

Reaction equation

HRID 1603238 reaction equation
[CH3:1][C@H:2]([NH:10][C:11](=[O:16])[C:12]([F:15])([F:14])[F:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:17][S:18](O)(=[O:20])=[O:19]>C(Cl)(Cl)Cl>[F:15][C:12]([F:13])([F:14])[C:11]([NH:10][C@@H:2]([CH3:1])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([S:18]([Cl:17])(=[O:20])=[O:19])=[CH:6][CH:5]=1)=[O:16]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 537678642,2,2-Trifluoro-N-[(2S)-1-phenylpropan-2-yl]acetamide

Product 1

HCID 53761610HCID 53761610, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2.0 g (8.64 mmol) of (S)-N-(1-methyl-2-phenylethyl)trifluoroacetamide (15) in 200 mL of chloroform was added 24 mL of chlorosulfonic acid dropwise at 0° C. The mixture was stirred at 0° C. for 4 hours. The reaction mixture was poured into 100 mL of ice water and extracted with 3×200 mL of chloroform. The organic layers were combined, dried over anhydrous sodium sulphate and evaporated to yield 2.58 g (7.82 mmol, 90%) of (S)-4-[2-[(trifluoroacetyl) amino]propyl]-benzenesulfonyl chloride (16) as a white solid. NMR, IR and MS data confirmed compound identity.

Workup

  1. extractionextracted with 3×200 mL of chloroform
  2. dry with materialdried over anhydrous sodium sulphate
  3. customevaporated

Sources & evidence

ORD record
ord-e320ac0f8dbb41fb8865cde201c4d352
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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