Ethyl chloroformate → Methyl 2-[(ethoxycarbonyl)amino]-5-ethylthiophene-3-carboxylate

HRID 1889298Notes

Reaction equation

HRID 1889298 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:11][CH3:12])=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8].Cl[C:14]([O:16][CH2:17][CH3:18])=[O:15]>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:14]([NH:1][C:2]1[S:3][C:4]([CH2:11][CH3:12])=[CH:5][C:6]=1[C:7]([O:9][CH3:10])=[O:8])=[O:15])[CH3:18]

Participants

4

Reactant 2

HCID 10928Ethyl chloroformateHCID 7370942-Amino-5-ethyl-3-thiophenecarboxylic acid methyl ester

Product 1

HCID 59351565Methyl 2-[(ethoxycarbonyl)amino]-5-ethylthiophene-3-carboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 2-amino-5-ethylthiophene-3-carboxylate (7.07 g), ethyl chloroformate (4.4 mL) and toluene (100 mL) was stirred at 100° C. for 3 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to give the title compound as colorless oil (9 g, 92%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f6cad9811457482fb2f981cfae7d4920
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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