Triethylamine → 2-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl isothiocyanate

HRID 380790Notes

Reaction equation

HRID 380790 reaction equation
[NH2:1][C:2]1[C:3]([Cl:22])=[CH:4][C:5]([F:21])=[C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])[CH:7]=1.C(N(CC)CC)C.[C:30](Cl)(Cl)=[S:31]>C1(C)C=CC=CC=1>[Cl:22][C:3]1[CH:4]=[C:5]([F:21])[C:6]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[CH:7][C:2]=1[N:1]=[C:30]=[S:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 186192573-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 183659632-Chloro-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-phenyl isothiocyanateYield 98%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-(trifluoromethyl)-2,4 (1H,3H)-pyrimidinedione (1.0 g, 2.96 mmol) in toluene is cooled to 0° C., treated sequentially with triethylamine (0.91 mL, 6.52 mmol) and thiophosgene (0.25 mL, 3.26 mmol), warmed to and stirred at room temperature for 5 hours, and filtered to remove solids. The resultant filtrate is concentrated in vacuo to give the title product as an orange solid (1.1 g, 98% yield) which is identified by 1H NMR spectral analysis.

Workup

  1. temperaturewarmed to and
  2. filtrationfiltered
  3. customto remove solids
  4. concentrationThe resultant filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-74321f3db0d04bb4b6697cdbdffd78b8
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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