Triethylamine → Phenyl phenylmethoxycarbonylamino chlorophosphate

HRID 2082327Notes

Reaction equation

HRID 2082327 reaction equation
[OH:1][NH:2][C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[P:20](Cl)([Cl:29])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]>C(OCC)C>[P:20]([Cl:29])([O:1][NH:2][C:3]([O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1)=[O:12])([O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13038Phosphorodichloridic acid, phenyl esterHCID 18907Benzyl hydroxycarbamate

Product 1

HCID 85654019Phenyl phenylmethoxycarbonylamino chlorophosphateYield 102.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of benzyl N-hydroxycarbamate (0.35 g, 2.1 mmol) and triethylamine (0.21 g, 2.1 mmol) in diethyl ether is cooled at 0° C. with stirring. To this is added a solution of phenyl dichlorophosphate (0.43 g, 2 mmol) in diethyl ether (1 ml). The resulting suspension is stirred at room temperature for 3 hours. It is then filtered and the solvents evaporated under reduced pressure to give 0.70 g of a colorless oil.

Workup

  1. stirringThe resulting suspension is stirred at room temperature for 3 hours
  2. filtrationIt is then filtered
  3. customthe solvents evaporated under reduced pressure

Sources & evidence

ORD record
ord-5195326196a64aa09c7ad34600815444
Source dataset
uspto-grants-1993_02
Patent number
US05189023

Reaction notes

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