Isocyanatocarbonyl chloride → HCID 86749499, compound

HRID 1418758Notes

Reaction equation

HRID 1418758 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][NH:6][C:7](=[O:30])[NH:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[C:18]([Cl:26])[CH:17]=2)[CH:12]=[CH:11][C:10]=1[N+:27]([O-:29])=[O:28])[CH3:2].[C:32](=[O:37])=[N:33][C:34](Cl)=[O:35]>C1(C)C=CC=CC=1>[Cl:26][C:18]1[CH:17]=[C:16]([O:15][C:13]2[CH:12]=[CH:11][C:10]([N+:27]([O-:29])=[O:28])=[C:9]([N:8]3[C:34](=[O:35])[NH:33][C:32](=[O:37])[N:6]([CH2:5][C:4]([O:3][CH2:1][CH3:2])=[O:31])[C:7]3=[O:30])[CH:14]=2)[CH:21]=[CH:20][C:19]=1[C:22]([F:23])([F:24])[F:25]

Participants

4

Reactant 2

HCID 119708Isocyanatocarbonyl chloride2×HCID 86751284HCID 86751284, compound

Product 1

HCID 86749499HCID 86749499, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of N-{{5-[(2-chloro-α,α,α-trifluoro-p-tolyl)oxy]-2-nitrophenyl}carbamoyl}glycine ethyl ester (75.0 g, 0.162 mol) and N-(chlorocarbonyl) isocyanate (35.0 g, 0.332 mol) in toluene is heated at 60° C. overnight, treated with additional N-(chlorocarbonyl) isocyanate (4.25 g), heated at 60° C. for 4 hours, cooled to room temperature and filtered to obtain a solid. The solid is washed with petroleum ether and dried to give the title product as a white solid which is identified by 1H and 13CNMR spectral analyses.

Workup

  1. temperatureheated at 60° C. for 4 hours
  2. temperaturecooled to room temperature
  3. filtrationfiltered
  4. customto obtain a solid
  5. washThe solid is washed with petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-077a0852e51541d89ca8b3b2f0476715
Source dataset
uspto-grants-1999_03
Patent number
US05883282

Reaction notes

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