Phosgene → HCID 54388472, compound

HRID 1419937Notes

Reaction equation

HRID 1419937 reaction equation
[C:1]([Cl:4])(Cl)=O.[CH2:5]([O:12][C:13]1[CH:24]=[CH:23][C:16]([C:17]([NH:19][CH2:20]CO)=[O:18])=[CH:15][CH:14]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>O1CCOCC1>[CH2:5]([O:12][C:13]1[CH:14]=[CH:15][C:16]([C:17]([NH:19][CH2:20][CH2:1][Cl:4])=[O:18])=[CH:23][CH:24]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 10825986Benzamide, N-(2-hydroxyethyl)-4-(phenylmethoxy)-

Product 1

HCID 54388472HCID 54388472, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Phosgene was bubbled through a suspension of 4-benzyloxy-N-(2-hydroxy-ethyl)-benzamide (22.49 g, 82.8 mmol) in dioxane (130 ml) until all the insoluble material had dissolved. Excess phosgene was removed by a stream of carbon dioxide. The solvent was removed at reduced pressure, and the residue was dried for 1 h. at 100° C. The crude product was recrystallized from ethyl acetate to yield 4-benzyloxy-N-(2-chloro-ethyl)-benzamide (16.3 g, 68%).

Workup

  1. dissolutionhad dissolved
  2. customExcess phosgene was removed by a stream of carbon dioxide
  3. customThe solvent was removed at reduced pressure
  4. customthe residue was dried for 1 h. at 100° C
  5. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-8411032a6d99496497fa972b19edd8f1
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

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