Chlorosulfonic acid → 5-Acetylamino-4-carbamoyl-3-methyl-thiophene-2-sulfonyl chloride

HRID 1049864Notes

Reaction equation

HRID 1049864 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([NH:9][C:10]1[S:11][CH:12]=[C:13]([CH3:18])[C:14]=1[C:15]([NH2:17])=[O:16])(=[O:8])[CH3:7]>>[C:6]([NH:9][C:10]1[S:11][C:12]([S:2]([Cl:1])(=[O:5])=[O:3])=[C:13]([CH3:18])[C:14]=1[C:15](=[O:16])[NH2:17])(=[O:8])[CH3:7]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 28077082-Acetylamino-4-methylthiophene-3-carboxylic acid amide

Product 1

HCID 1177039655-Acetylamino-4-carbamoyl-3-methyl-thiophene-2-sulfonyl chloride

Conditions

Temperature
40 °C

Procedure

Neat ClSO3H (6.7 mL, 100 mmol) is cooled to 0° C. 2-acetylamino-4-methyl-thiophene-3-carboxylic acid amide (1.98 g, 10 mmol) is added in portions over a period of 15 min, and the mixture is stirred at 40° C. for 3 h. The mixture is cooled down to room temperature and poured slowly onto ice cold water. The resulting suspension is washed twice with EtOAc, the combined organic fractions are dried over MgSO4, filtered and evaporated to yield the desired product which is used as such.

Workup

  1. temperatureThe mixture is cooled down to room temperature
  2. additionpoured slowly onto ice cold water
  3. washThe resulting suspension is washed twice with EtOAc
  4. dry with materialthe combined organic fractions are dried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-61d5b89f45a94d9bb3b2fe2000a3cf60
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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