Phosgene → [4-(Benzyloxy)-3-isocyanatophenyl](pyridin-2-yl)methanone

HRID 1287848Notes

Reaction equation

HRID 1287848 reaction equation
[C:1](Cl)(Cl)=[O:2].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:15]([NH2:27])[CH:14]=1)=[O:12]>C1(C)C=CC=CC=1>[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[C:15]([N:27]=[C:1]=[O:2])[CH:14]=1)=[O:12]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 53880974[3-Amino-4-(benzyloxy)phenyl](pyridin-2-yl)methanone

Product 1

HCID 54132362[4-(Benzyloxy)-3-isocyanatophenyl](pyridin-2-yl)methanone

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 40 g (0.41 mol) of phosgene in 150 ml of toluene is held at 25° C while a mixture of (52.5 mmol) of 3-amino-4-benzyloxyphenyl 2-pyridyl ketone and 300 ml of toluene is added slowly. The mixture is refluxed for 30 minutes and then is concentrated to give 4-benzyloxy-3-isocyanatophenyl 2-pyridyl ketone.

Workup

  1. additionis added slowly
  2. temperatureThe mixture is refluxed for 30 minutes
  3. concentrationis concentrated

Sources & evidence

ORD record
ord-94d27eb0169c4cbe86d2c3c9546a141b
Source dataset
uspto-grants-1976_10
Patent number
US03985887

Reaction notes

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