Chlorosuccinimide → 5-Chloro-N-methoxy-N-methyl-3-thiophenecarboxamide

HRID 626106Notes

Reaction equation

HRID 626106 reaction equation
[CH3:1][O:2][N:3]([CH3:11])[C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[O:5].[Cl:12]N1C(=O)CCC1=O>CC(O)=O>[Cl:12][C:9]1[S:8][CH:7]=[C:6]([C:4]([N:3]([O:2][CH3:1])[CH3:11])=[O:5])[CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 22489894N-methoxy-N-methylthiophene-3-carboxamide

Product 1

HCID 876931115-Chloro-N-methoxy-N-methyl-3-thiophenecarboxamideYield 50.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of N-methoxy-N-methylthiophene-3-carboxamide (5.0 g, 1.0 eq, prepared from Example 12 step A) in 50 mL CH3COOH was added N-chlorosuccinimide (3.88 g, 1.0 eq). The mixture was then reflux at 120° C. for 4 h. After quenching with water, the mixture was extracted with ethyl acetate. The extract was washed with brine, dried, concentrated, and purified by column chromatography to get 3.0 g desired product (40% yield).

Workup

  1. customAfter quenching with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. custompurified by column chromatography

Sources & evidence

ORD record
ord-a4771230c0664c0080f603dfa08806ab
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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