Pyridine → HCID 86608143, compound

HRID 1094974Notes

Reaction equation

HRID 1094974 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].N1C=CC=CC=1.CO[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][C:29]=1OC)[C:24](Cl)=[O:25].[CH2:32](Cl)[Cl:33]>>[CH2:10]([O:9][C:7]([C:6]1([CH2:32][Cl:33])[C:5]([CH3:12])=[CH:4][S:3][CH:2]1[NH:1][C:24](=[O:25])[C:23]1[CH:27]=[CH:28][CH:29]=[CH:21][CH:22]=1)=[O:8])[CH3:11]

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 77070Veratroyl chloride2×HCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate2×

Product 1

HCID 86608143HCID 86608143, compound

Conditions

Temperature
0 °C

Procedure

Ethyl 2-amino-4-methylthiophene-3-carboxylate (compound A) (3.0 g) was dissolved in anhydrous methylene chloride (40.0 ml). Subsequently, pyridine (1.5 ml) and 3-(chloromethyl)benzoyl chloride (compound B) (2.8 ml) were added to the solution, and the mixture was stirred at 0° C. for one hr. After the completion of the reaction, distilled water was added, and the mixture was subjected to separatory extraction with chloroform. The organic layer was washed with saturated brine, was dried over sodium sulfate, and was then concentrated to give 2-(3-chloromethyl-benzoylamino-4-methyl-thiophene-3-carboxylic acid ethyl ester as a useful intermediate (3.80 g, yield 70%).

Workup

  1. customAfter the completion of the reaction
  2. distillationdistilled water
  3. additionwas added
  4. extractionthe mixture was subjected to separatory extraction with chloroform
  5. washThe organic layer was washed with saturated brine
  6. dry with materialwas dried over sodium sulfate
  7. concentrationwas then concentrated

Sources & evidence

ORD record
ord-ab7f2862b9af48de90d03f1fab5b41a2
Source dataset
uspto-grants-2012_03
Patent number
US08134015B2

Reaction notes

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