Chlorosulfonic acid → 5-(2-Acetylamino-4-methyl-thiazol-5-yl)-2-methoxy-benzenesulfonyl chloride

HRID 2247336Notes

Reaction equation

HRID 2247336 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[S:18][C:17]([NH:19][C:20](=[O:22])[CH3:21])=[N:16][C:15]=2[CH3:23])=[CH:10][CH:9]=1>C(Cl)Cl>[C:20]([NH:19][C:17]1[S:18][C:14]([C:11]2[CH:10]=[CH:9][C:8]([O:7][CH3:6])=[C:13]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:12]=2)=[C:15]([CH3:23])[N:16]=1)(=[O:22])[CH3:21]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 85861728HCID 85861728, compound

Product 1

HCID 865984085-(2-Acetylamino-4-methyl-thiazol-5-yl)-2-methoxy-benzenesulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To chlorosulfonic acid (25 ml, excess), cooled at −10° C., is added portionwise a suspension of N-[5-(4-methoxy-phenyl)-4-methyl-thiazol-2-yl]-acetamide (Example 31a) (1.0 g, 3.8 mmol) in DCM (10 ml). The temperature is kept below 0° C. throughout the addition. The reaction mixture is left to warm up to room temperature. After 2 hours, the reaction mixture is poured carefully onto ice (500 ml). Once the ice is melted, the aqueous layer is extracted with DCM (3×200 ml). The combined organic layers are washed with brine (150 ml), dried over MgSO4, filtered and concentrated to afford 5-(2-acetylamino-4-methyl-thiazol-5-yl)-2-methoxybenzene-sulfonyl chloride.

Workup

  1. additionis added portionwise
  2. additionThe temperature is kept below 0° C. throughout the addition
  3. waitThe reaction mixture is left
  4. additionthe reaction mixture is poured carefully onto ice (500 ml)
  5. extractionthe aqueous layer is extracted with DCM (3×200 ml)
  6. washThe combined organic layers are washed with brine (150 ml)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d86a877ec9e5464a9875e85a9bb1c7d5
Source dataset
uspto-grants-2010_03
Patent number
US07687637B2

Reaction notes

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