Thiophosgene → 4,6-Bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl isothiocyanate

HRID 1254838Notes

Reaction equation

HRID 1254838 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]([F:13])([F:12])[F:11])[CH:5]=[C:4]([O:14][CH2:15][C:16]([F:19])([F:18])[F:17])[N:3]=1.[C:20](Cl)(Cl)=[S:21]>O1CCOCC1>[F:11][C:10]([F:12])([F:13])[CH2:9][O:8][C:6]1[CH:5]=[C:4]([O:14][CH2:15][C:16]([F:19])([F:17])[F:18])[N:3]=[C:2]([N:1]=[C:20]=[S:21])[N:7]=1

Participants

4

Reactant 2

HCID 10040ThiophosgeneHCID 43342632-Amino-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine

Product 1

HCID 576518094,6-Bis(2,2,2-trifluoroethoxy)pyrimidin-2-yl isothiocyanateYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-Amino-4,6-bis(2,2,2-trifluoroethoxy)pyrimidine (20.0 g, 68.7 mmol) was added to a solution of thiophosgene (15.7 mL, 206 mmol) in anhydrous dioxane (100 mL) under an N2 atmosphere. The resulting solution was heated to reflux. After 18 h the heat was removed and the reaction cooled to room temperature. The dioxane was evaporated to give a dark oil. The dark oil was distilled to afford the product as a light yellow oil (13.7 g, 60% yield); by 83-86° C., (ca 0.2 mmHg): 1H NMR (CDCl3) δ 6.24 (s 1H), 4.78 (q, 4H, J=8.2 Hz); GCMS (EI, 70 eV) m/z 333 (M+).

Workup

  1. temperatureThe resulting solution was heated to reflux
  2. customAfter 18 h the heat was removed
  3. customThe dioxane was evaporated
  4. customto give a dark oil
  5. distillationThe dark oil was distilled

Sources & evidence

ORD record
ord-b88d56bec4494bd482efadcec055e2b2
Source dataset
uspto-grants-2013_06
Patent number
US08455649B2

Reaction notes

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