Triethylamine → HCID 11736989, compound

HRID 362446Notes

Reaction equation

HRID 362446 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH2:10])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18]1([O:24][C:25](Cl)=[O:26])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:25](=[O:26])[O:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 754524-Methoxybenzylamine

Product 1

HCID 11736989HCID 11736989, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-methoxybenzenemethanamine (72.7 g) and triethylamine (83.6 ml) in CH2Cl2 (750 ml) was cooled on an ice-bath. Phenylchloroformate (91.4 g) was added dropwise and the reaction mixture was stirred at RT. The reaction mixture was washed three times with water and the precipitate was filtered off. The organic layer was separated, washed three times with a 5% aqueous NaHCO3 solution, dried (MgSO4), filtered and the solvent was evaporated. The precipitate was stirred in boiling diethyl ether (300 ml), filtered off and dried, yielding 84.4 g (65.5%) of phenyl [(4-methoxyphenyl)methyl]carbamate (interm. 2).

Workup

  1. washThe reaction mixture was washed three times with water
  2. filtrationthe precipitate was filtered off
  3. customThe organic layer was separated
  4. washwashed three times with a 5% aqueous NaHCO3 solution
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. stirringThe precipitate was stirred
  9. filtrationfiltered off
  10. customdried

Sources & evidence

ORD record
ord-ac97008a1f6540ea9d37c1b64c785471
Source dataset
uspto-grants-1999_02
Patent number
US05869515

Reaction notes

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