Phosgene → Isopropyl3-(2-chloro-4-fluoro-5-isocyanatophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

HRID 975766Notes

Reaction equation

HRID 975766 reaction equation
[NH2:1][C:2]1[C:3]([F:26])=[CH:4][C:5]([Cl:25])=[C:6]([N:8]2[C:13](=[O:14])[N:12]([CH3:15])[C:11](=[O:16])[N:10]([CH2:17][C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[C:9]2=[O:24])[CH:7]=1.[C:27](Cl)(Cl)=[O:28]>C1(C)C=CC=CC=1>[CH:21]([O:20][C:18](=[O:19])[CH2:17][N:10]1[C:11](=[O:16])[N:12]([CH3:15])[C:13](=[O:14])[N:8]([C:6]2[CH:7]=[C:2]([N:1]=[C:27]=[O:28])[C:3]([F:26])=[CH:4][C:5]=2[Cl:25])[C:9]1=[O:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 6371PhosgeneHCID 57313385isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Product 1

HCID 57228591Isopropyl3-(2-chloro-4-fluoro-5-isocyanatophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of isopropyl 3-(5-amino-2-chloro-4-fluorophenyl)tetrahydro-5-methyl-2,4,6-trioxo-s-triazine-1(2H)-acetate (4.0 g, 0.0103 mol) in toluene is treated with a 1.93M solution of phosgene in toluene (19 mL), refluxed for 3 hours, cooled, partially concentrated in vacuo, diluted with toluene, partially concentrated in vacuo, diluted with toluene and concentrated in vacuo to give the title product as a yellow foam which is identified by 1H NMR spectral analysis.

Workup

  1. temperaturerefluxed for 3 hours
  2. temperaturecooled
  3. concentrationpartially concentrated in vacuo
  4. additiondiluted with toluene
  5. concentrationpartially concentrated in vacuo
  6. additiondiluted with toluene
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e082d3eee8024ee78ab76e31ccf03242
Source dataset
uspto-grants-1997_03
Patent number
US05610120

Reaction notes

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