Methyl chloroformate → N-methoxycarbonyl-N-phenyl-7-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-6-carboxylic acid methyl ester

HRID 1081964Notes

Reaction equation

HRID 1081964 reaction equation
[C:1]1([N:7]=[CH:8][C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH3:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:15]([O:19][CH3:20])(=[O:18])[CH:16]=[CH2:17].C(N(C(C)C)CC)(C)C.Cl[C:31]([O:33][CH3:34])=[O:32]>C1(C)C(C)=CC=CC=1>[CH3:20][O:19][C:15]([CH:16]1[CH:8]([N:7]([C:31]([O:33][CH3:34])=[O:32])[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:9]2[S:10][CH:11]=[CH:12][C:13]=2[CH2:14][CH2:17]1)=[O:18]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 7294Methyl AcrylateHCID 81531DiisopropylethylamineHCID 9273143-Methylthiophene-2-aldehyde phenylimine

Product 1

HCID 15389403N-methoxycarbonyl-N-phenyl-7-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-6-carboxylic acid methyl esterYield 96.9%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

3-methylthiophene-2-aldehyde phenylimine (50 g, 0.248 mol), methyl acrylate (224 ml, 2.48 mol) and diisopropyl ethylamine (173 ml, 0.993 mol) were mixed in xylene (1000 ml) and stirred under ice cooling. Methyl chloroformate (76.8 ml, 0.993 mol) was added to the mixture. After completing the addition, the reaction mixture was heated under reflux for 3 hours and then allowed to cool to room temperature. The reaction mixture was washed with an aqueous solution of sodium hydrogen carbonate and an aqueous solution of sodium chloride and dried over sodium sulfate. After distilling off the solvent, 83 g of crude N-methoxycarbonyl-N-phenyl-7-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-6-carboxylic acid methyl ester was obtained.

Workup

  1. additionthe addition
  2. temperaturethe reaction mixture was heated
  3. temperatureunder reflux for 3 hours
  4. washThe reaction mixture was washed with an aqueous solution of sodium hydrogen carbonate
  5. dry with materialan aqueous solution of sodium chloride and dried over sodium sulfate
  6. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-bc32a0f7cf624b1b9f2deafa190de870
Source dataset
uspto-grants-1996_12
Patent number
US05587486

Reaction notes

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