Ethyl chloroformate → HCID 59535737, compound

HRID 1660920Notes

Reaction equation

HRID 1660920 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:9]=2[C:10]=1[NH2:11])=[O:5])[CH3:2].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19].C([O-])([O-])=O.[K+].[K+]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:9]=2[C:10]=1[NH:11][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 617363ethyl 3-amino-5-chlorobenzofuran-2-carboxylate

Product 1

HCID 59535737HCID 59535737, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-amino-5-chloro-benzofuran-2-carboxylic acid ethyl ester (2.8 g, 11.7 mmol) in benzene (35 mL) was added ethyl chloroformate (1.3 mL, 14.0 mmol) followed by K2CO3 (4.5 g, 35.1 mmol). After heating at reflux for 14 h, the mixture was filtered, washing with benzene. The filtrate was concentrated to afford the desired product (100%), which was used in the next step without further purification. 1H NMR (CDCl3): 8.69 (s, 1H), 8.45 (s, 1H), 7.47-7.39 (m, 2H), 4.48 (q, J=7.1 Hz, 2H), 4.30 (q, J=7.1 Hz, 2H), 1.55 (t, J=7.1 Hz, 3H), 1.35 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 14 h
  3. filtrationthe mixture was filtered
  4. washwashing with benzene
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-d11badb05dcc4f37ae385a0d669a6743
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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