Thionyl Chloride → HCID 21935964, compound

HRID 1242351Notes

Reaction equation

HRID 1242351 reaction equation
[CH:1]1([C:4]2[C:9]([CH2:10]O)=[CH:8][N:7]=[C:6]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=3)[N:5]=2)[CH2:3][CH2:2]1.O=S(Cl)[Cl:24]>C(Cl)Cl>[Cl:24][CH2:10][C:9]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[N:7][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21935665HCID 21935665, compound

Product 1

HCID 21935964HCID 21935964, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.300 g (1.019 mmol) of the above prepared [4-cyclopropyl-2-(3-trifluoromethyl-phenyl)-pyrimidin-5-yl]-methanol was dissolved in 5 ml of CH2Cl2 and treated at 0° C. with 0.15 ml (2 eq.) of SOCl2. The reaction mixture was kept at 0° C. for 5 Min. and at ambient temperature for 30 Min. Pouring onto crashed ice/NaHCO3, twofold extraction with AcOEt, washing with water, drying over sodium sulfate, and evaporation of the solvents gave 0.315 g of pure title compound as white solid of mp. 92–95° C.

Workup

  1. customwas kept at 0° C. for 5 Min
  2. customat ambient temperature
  3. additionPouring
  4. extractionice/NaHCO3, twofold extraction with AcOEt
  5. washwashing with water
  6. dry with materialdrying over sodium sulfate, and evaporation of the solvents

Sources & evidence

ORD record
ord-ab451d983b8a403d82217c8304932383
Source dataset
uspto-grants-2006_10
Patent number
US07115611B2

Reaction notes

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