Chlorosuccinimide → 2-Acetylamino-5-chloro-4-methyl-thiophene-3-carboxylic acid amide

HRID 1049863Notes

Reaction equation

HRID 1049863 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH3:13])[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2].C1C(=O)N([Cl:21])C(=O)C1>CO>[C:1]([NH:4][C:5]1[S:6][C:7]([Cl:21])=[C:8]([CH3:13])[C:9]=1[C:10]([NH2:12])=[O:11])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 28077082-Acetylamino-4-methylthiophene-3-carboxylic acid amide

Product 1

HCID 1177040292-Acetylamino-5-chloro-4-methyl-thiophene-3-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

2-acetylamino-4-methylthiophene-3-carboxylic acid amide (2 g, 10.1 mmol) is dissolved in MeOH (40 mL). NCS (1.47 g, 11.1 mmol) is added and the resulting suspension is stirred at 60° C. for 1 h. The mixture is then concentrated under vacuo, the obtained residue is dissolved in DCM and washed with aqueous NaHCO3. The organic phase is then dried over MgSO4, filtered and concentrated under vacuo to yield the desired compound which is used as such.

Workup

  1. concentrationThe mixture is then concentrated under vacuo
  2. dissolutionthe obtained residue is dissolved in DCM
  3. washwashed with aqueous NaHCO3
  4. dry with materialThe organic phase is then dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-a27b7dab860046f9b9951ce9b7b5c619
Source dataset
uspto-grants-2016_07
Patent number
US09382254B2

Reaction notes

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