Methyl chloroformate → HCID 178517434, compound

HRID 2402522Notes

Reaction equation

HRID 2402522 reaction equation
[CH:1]1([Mg]Cl)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:9][C:10]1[CH:17]=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].Cl[C:19](OC)=[O:20]>CCOCC>[CH:1]1([C:12]2[C:11]3[C:10](=[CH:17][CH:16]=[CH:15][CH:14]=3)[NH:9][C:19](=[O:20])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 729132-AminobenzonitrileHCID 178478990HCID 178478990, compound

Product 1

HCID 178517434HCID 178517434, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a dried round-bottomed flask containing cyclohexylmagnesium chloride (26 mL, 51 mmol) in anhydrous ether (10 mL) was added dropwise a solution of 2-aminobenzonitrile (2.0 g, 17 mmol) in anhydrous ether. The mixture was stirred at rt for 2 h, then cooled to 0° C., and a solution of methyl chloroformate (2.6 mL, 34 mmol) in dry ether (10 mL) was added. The reaction mixture was returned to rt and stirred for 2 d. The reaction was quenched with 1 N hydrochloric acid and stirred for 30 min. The precipitate that formed was collected by vacuum filtration, washed with ethyl acetate and dried to give 4-cyclohexylquinazolin-2(1H)-one (545 mg, 14%) as a tan solid.

Workup

  1. temperaturecooled to 0° C.
  2. customwas returned to rt
  3. stirringstirred for 2 d
  4. customThe reaction was quenched with 1 N hydrochloric acid
  5. stirringstirred for 30 min
  6. customThe precipitate that formed
  7. filtrationwas collected by vacuum filtration
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-4bc015ee3b834a35bf7f8d966232b1a9
Source dataset
uspto-grants-2014_08
Patent number
US08796294B2

Reaction notes

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