Chlorosulfonic acid → 5-(2-Acetamido-4-methylthiazol-5-yl)furan-2-sulfonyl chloride

HRID 2386179Notes

Reaction equation

HRID 2386179 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:10][C:9]([NH:11][C:12](=[O:14])[CH3:13])=[N:8][C:7]=1[CH3:15].[S:16]([Cl:20])(=O)(=[O:18])[OH:17]>>[C:12]([NH:11][C:9]1[S:10][C:6]([C:2]2[O:1][C:5]([S:16]([Cl:20])(=[O:18])=[O:17])=[CH:4][CH:3]=2)=[C:7]([CH3:15])[N:8]=1)(=[O:14])[CH3:13]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 59362180N-(5-(furan-2-yl)-4-methylthiazol-2-yl)acetamide

Product 1

HCID 593621765-(2-Acetamido-4-methylthiazol-5-yl)furan-2-sulfonyl chloride

Procedure

To N-(5-(furan-2-yl)-4-methylthiazol-2-yl)acetamide (0.443 g) under an ice-salt bath was added sulfurochloridoic acid (ClSO3H, 5 ml). After 30 min, the reaction was poured into crushed ice (150 g). Extraction with dichloromethane (3×30 ml), drying and concentration gave 5-(2-acetamido-4-methylthiazol-5-yl)furan-2-sulfonyl chloride (0.359 g) that was used directly for next step.

Workup

  1. additionthe reaction was poured
  2. extractionExtraction with dichloromethane (3×30 ml)
  3. customdrying
  4. concentrationconcentration

Sources & evidence

ORD record
ord-0c5e5284cfa54de9a260e7292472f86f
Source dataset
uspto-grants-2012_09
Patent number
US08268818B2

Reaction notes

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