Phosgene → 4-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl chloroformate

HRID 1636445Notes

Reaction equation

HRID 1636445 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:25])=[C:6]([CH2:8][N:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[O:11][C:10]2=[O:24])[CH:7]=1.[C:26](Cl)([Cl:28])=[O:27]>C1(C)C=CC=CC=1>[Cl:28][C:26]([O:25][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[CH2:8][N:9]1[N:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)[O:11][C:10]1=[O:24])=[O:27]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 10474339Bms-191011

Product 1

HCID 154628094-Chloro-2-[[5-[4-(trifluoromethyl)phenyl]-2,3-dihydro-2-oxo-1,3,4-oxadiazol-3-yl]methyl]phenyl chloroformate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A stirred suspension of 3-[(5-chloro-2-hydroxyphenyl)methyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazol-2(3H)-one (1 g, 2.69 mmol) and BnPh3PCI (25 mg) in 1.9 molar toluene solution of phosgene (15 mL) was heated at 120° C. overnight in a sealed tube. After removal of excess phosgene, the toluene solution was rotary evaporated to dryness to afford the chlorotormate product as a white semi-solid (1.18 g).

Workup

  1. customAfter removal of excess phosgene
  2. customthe toluene solution was rotary evaporated to dryness

Sources & evidence

ORD record
ord-468259b53f214cf7abd8f9422648cb9c
Source dataset
uspto-grants-2000_03
Patent number
US06034113

Reaction notes

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