Chlorosulfonic acid → 4-(2-Acetamido-1,3-thiazol-4-yl)benzene-1-sulfonyl chloride

HRID 879707Notes

Reaction equation

HRID 879707 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:12][C:13](=[O:15])[CH3:14])[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:16][S:17](O)(=[O:19])=[O:18]>>[C:13]([NH:12][C:9]1[S:10][CH:11]=[C:7]([C:1]2[CH:2]=[CH:3][C:4]([S:17]([Cl:16])(=[O:19])=[O:18])=[CH:5][CH:6]=2)[N:8]=1)(=[O:15])[CH3:14]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 227306N-(4-Phenyl-1,3-thiazol-2-yl)ethanimidic acid

Product 1

HCID 583273234-(2-Acetamido-1,3-thiazol-4-yl)benzene-1-sulfonyl chloride

Procedure

N-(4-phenyl-thiazol-2-yl)-acetamide was added to chlorosulfonic acid (5 eq) at 0° C. and allowed to warm to room temperature. The mixture was heated at 70° C. for 1 h and carefully poured into ice. The solid was filtered, washed with water and dried under vacuum to give 4-(2-acetylamino-thiazol-4-yl)-benzenesulfonyl chloride. Characterized by derivatization as N-[4-(4-Isobutylsulfamoyl-phenyl)-thiazol-2-y]-acetamide, 1H NMR (400 MHz, CD3OD) 8.08 (d, 2H), 7.85 (d, 2H), 7.58 (s, 1H), 2.66 (d, 2H), 2.22 (s, 3H), 1.7 (m, 1H), 0.87 (d, 6H). LCMS (m/z): 354.

Workup

  1. temperatureThe mixture was heated at 70° C. for 1 h
  2. additioncarefully poured into ice
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-aef238e4f5454dc48a1d3c6b3ff1d09d
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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