Chlorosulfonic acid → HCID 86655211, compound

HRID 1256086Notes

Reaction equation

HRID 1256086 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][CH2:13][C:14](=[O:16])[CH3:15])[CH:7]=1)=[O:4].[OH:19][S:20]([Cl:23])(=O)=[O:21]>C(Cl)Cl>[O:16]=[C:14]([CH3:15])[CH2:13][CH2:12][C:8]1[CH:7]=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:17])([F:18])[F:1])[CH:11]=[CH:10][C:9]=1[S:20]([Cl:23])(=[O:21])=[O:19]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 86655209HCID 86655209, compound

Product 1

HCID 86655211HCID 86655211, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2,2,2-trifluoro-N-(3-(3-oxobutyl)phenyl)acetamide (2 g, 8 mmol) was added HOSO2Cl (9 g, 77 mmol) dropwise at 0° C. The mixture was stirred at r.t. for 3 hrs. The reaction mixture was diluted with DCM and washed with water, the organics was dried over Na2SO4 and concentrated to give 2-(3-oxobutyl)-4-(2,2,2-trifluoroacetamido)benzene-1-sulfonyl chloride (1.5 g, yield 54%). 1H NMR: (400 MHz, CDCl3) δ 8.05 (s, 1H), 7.76 (d, 1H), 7.70 (t, 1H), 7.63 (d, 1H), 3.31 (t, 2H), 2.82 (t, 2H), 2.14 (s, 3H).

Workup

  1. washwashed with water
  2. dry with materialthe organics was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cd54dabd07ff4610ae60533cef979ed4
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

Loading…