Methyl chloroformate → HCID 13813704, compound

HRID 652591Notes

Reaction equation

HRID 652591 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].C([O-])([O-])=O.[K+].[K+].[NH2:12][C:13]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:14]=1[C:15]#[N:16]>C(Cl)(Cl)Cl>[C:15]([C:14]1[C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:13]=1[NH:12][C:2](=[O:3])[O:4][CH3:5])#[N:16]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 11430Potassium CarbonateHCID 13813702HCID 13813702, compound

Product 1

HCID 13813704HCID 13813704, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl chloroformate (18.6 g, 19.7 mmol) was added to a suspension of K2CO3 (2.71 g, 19.6 mmol) and 2-amino-5,6-dimethoxybenzonitrile (7.0 g, 39.3 mmol) in 70 ml of CHCl3. The resulting mixture was heated at reflux for 2 hours before using filtered and evaporated to a residual solid. Recrystallization of the crude material from MeOH yielded 4.64 g (50.2% of product in good purity.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. filtrationbefore using filtered
  4. customevaporated to a residual solid
  5. customRecrystallization of the crude material from MeOH

Sources & evidence

ORD record
ord-72e94d7e81784d39a481b56de5c7f401
Source dataset
uspto-grants-1987_06
Patent number
US04672116

Reaction notes

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