Ammonium Chloride → 2-[(4-Chlorophenyl)carbonyl]cyclopropanecarbonitrile

HRID 561412Notes

Reaction equation

HRID 561412 reaction equation
Cl[Mg][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Br-].[C:10]([CH:12]1[CH2:14][CH:13]1[C:15](N(OC)C)=[O:16])#[N:11].[Cl-:21].[NH4+]>C(OCC)C.O1CCCC1>[Cl:21][C:3]1[CH:8]=[CH:7][C:6]([C:15]([CH:13]2[CH2:14][CH:12]2[C:10]#[N:11])=[O:16])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 583925062-Cyano-N-methoxy-N-methylcyclopropanecarboxamideHCID 178419578HCID 178419578, compound

Product 1

HCID 583922662-[(4-Chlorophenyl)carbonyl]cyclopropanecarbonitrile

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

3.5 ml (3.50 mmol) of a 1N solution of chlorophenylmagnesium bromide in diethyl ether were introduced into 5 ml of THF at RT under argon, a solution of 490 mg (3.18 mmol) of the compound from Example 73A in 5 ml of tetrahydrofuran was added, and the mixture was heated under reflux for 2 h. Saturated aqueous ammonium chloride solution was added, two extractions with diethyl ether were carried out, and the combined organic phases were dried over sodium sulfate, filtered and concentrated. 714 mg of the title compound with a purity of 54% (59% of theory) were obtained and were reacted without further purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 h
  3. extractiontwo extractions with diethyl ether
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6672f1da13b14793aea2b1a8292edd69
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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