Diphosgene → HCID 86690139, compound

HRID 1184347Notes

Reaction equation

HRID 1184347 reaction equation
[O:1]=[C:2](Cl)OC(Cl)(Cl)Cl.[F:9][C:10]1([F:33])[O:15][C:14]2[CH:16]=[C:17]([F:28])[C:18]([NH:20][NH:21][C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][C:13]=2[N:12]([CH2:29][C:30]#[CH:31])[C:11]1=[O:32]>C1(C)C=CC=CC=1>[CH:14]([O:15][CH:10]([CH3:11])[CH3:2])([CH3:16])[CH3:13].[C:23]([C:22]1[O:27][C:2](=[O:1])[N:20]([C:18]2[C:17]([F:28])=[CH:16][C:14]3[O:15][C:10]([F:9])([F:33])[C:11](=[O:32])[N:12]([CH2:29][C:30]#[CH:31])[C:13]=3[CH:19]=2)[N:21]=1)([CH3:24])([CH3:25])[CH3:26]

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 86690138HCID 86690138, compound

Product 2

HCID 7914Diisopropyl EtherHCID 86690139HCID 86690139, compoundYield 140.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Diphosgene (0.445 ml, 3.69 mmol) was added dropwise to a stirred solution of N′-(2,2,7-trifluoro-3-oxo-4-(prop-2-ynyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)pivalohydrazide (1311 mg, 3.69 mmol) in dry toluene (30 ml) at room temperature under nitrogen. The resulting mixture was stirred at reflux for 4 hours. It was then cooled to room temperature and evaporated in vacuo to yield 1.7 g of crude product. Trituration of this with diisopropyl ether afforded 990 mg of the title compound as a white powder (purity>95%).

Workup

  1. temperatureat reflux for 4 hours
  2. customevaporated in vacuo
  3. customto yield 1.7 g of crude product

Sources & evidence

ORD record
ord-506de7ec987c4124877484545941bf6c
Source dataset
uspto-grants-2014_03
Patent number
US08669208B2

Reaction notes

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