Phosphorus oxychloride → HCID 60204633, compound

HRID 2267457Notes

Reaction equation

HRID 2267457 reaction equation
[S:1]1[C:5]([C:6]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][N:9]=[C:8](O)[N:7]=2)=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2.P(Cl)(Cl)([Cl:23])=O>>[S:1]1[C:5]([C:6]2[C:11]([C:12]([F:15])([F:14])[F:13])=[CH:10][N:9]=[C:8]([Cl:23])[N:7]=2)=[CH:4][C:3]2[CH:17]=[CH:18][CH:19]=[CH:20][C:2]1=2

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517754HCID 178517754, compound

Product 1

HCID 60204633HCID 60204633, compound

Conditions

Temperature
100 °C

Procedure

4-(Benzo[b]thiophen-2-yl)-5-(trifluoromethyl)pyrimidin-2-ol (0.28 g, 0.94 mmol) was treated with phosphorous oxychloride (6 mL) and the mixture was heated to 100° C. overnight. The volatiles were removed in vacuo and residual phosphorous oxycloride was azeotroped with toluene. The resulting residue was dissolved in chloroform, washed successively with cold water, saturated aqueous solution of sodium bicarbonate, water again and brine. The organic solution was dried with sodium sulfate and passed through a plug of silica gel. The filtrate was concentrated to yield a yellow solid (0.2 g). MS (M+H)+ 315.

Workup

  1. customThe volatiles were removed in vacuo and residual phosphorous oxycloride
  2. customwas azeotroped with toluene
  3. dissolutionThe resulting residue was dissolved in chloroform
  4. washwashed successively with cold water, saturated aqueous solution of sodium bicarbonate, water again
  5. dry with materialThe organic solution was dried with sodium sulfate
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-5947866527b44cd7b02e005f28688140
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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