Ethyl chloroformate → HCID 59535737, compound

HRID 2102831Notes

Reaction equation

HRID 2102831 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-841890a92e2b4c35ba5aaf1bbd7d5f08
Source dataset
uspto-grants-2009_08
Patent number
US07576092B2

Reaction notes

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