Hydrochloric Acid → N-benzyl-N-methylcarbamoyl chloride

HRID 1158436Notes

Reaction equation

HRID 1158436 reaction equation
N1C=CC=CC=1.[CH3:7][NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)(OC(Cl)(Cl)Cl)[O:17][C:18]([Cl:21])(Cl)Cl.Cl>C(Cl)Cl>[CH2:9]([N:8]([CH3:7])[C:18]([Cl:21])=[O:17])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7669N-MethylbenzylamineHCID 94429Triphosgene

Product 1

HCID 10464985N-benzyl-N-methylcarbamoyl chloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At −78° C. pyridine (1.25 mL, 15.5 mmol) followed by methyl benzylamine (2.0 mL, 15.5. mmol) are added to a solution of bis(trichloromethyl) carbonate (1.55 g, 5.2 mmol) in CH2Cl2 (20 mL). The reaction mixture is allowed to warm to RT and stirred for another 1.5 h. For workup 1N HCl is added to the yellow suspension and the mixture is extracted with ethyl acetate. Drying (Na2SO4) of the combined organic exctracts, filtration and evaporation of the solvent affords the title compound. MS (LC-MS): [M+H]+=184.1. tR (HPLC, Waters Symmetry C18 column, 20-95% CH3CN/H2O/3.5 min, 95% CH3CN/H2O, 2 min, CH3CN and H2O containing 0.1% TFA, flow: 0.6 mL/min): 3.84 min.

Workup

  1. customAt −78° C.
  2. extractionthe mixture is extracted with ethyl acetate
  3. customDrying
  4. filtration(Na2SO4) of the combined organic exctracts, filtration and evaporation of the solvent

Sources & evidence

ORD record
ord-4142003187f249e9a9d2daa207c288d2
Source dataset
uspto-grants-2010_10
Patent number
US07807709B2

Reaction notes

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