Phosphorus oxychloride → 3-(4-Chloro-2-pyrimidinyl)benzaldehyde

HRID 1380053Notes

Reaction equation

HRID 1380053 reaction equation
C([O:3][CH:4](OCC)[C:5]1[CH:6]=[C:7]([C:11]2[NH:16][C:15](=O)[CH:14]=[CH:13][N:12]=2)[CH:8]=[CH:9][CH:10]=1)C.P(Cl)(Cl)([Cl:23])=O>>[Cl:23][C:15]1[CH:14]=[CH:13][N:12]=[C:11]([C:7]2[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=2)[CH:4]=[O:3])[N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 13590395HCID 13590395, compound

Product 1

HCID 135903783-(4-Chloro-2-pyrimidinyl)benzaldehyde

Procedure

A 5.3 g portion of 2-(3-diethoxymethylphenyl)- 4(3H)-pyrimidinone and 30 ml of phosphorous oxychloride was heated on a steam bath overnight. The excess phosphorous oxychloride was removed under vacuum and the residue taken up in chloroform and passed through a hydrous magnesium silicate pad. Evaporation of the filtrate left 3.1 g of residue which had two spots by TLC (chloroform-silica gel). Trituration of the residue with ether gave 0.4 g of 3-(4-chloro-2-pyrimidinyl)benzaldehyde, mp 136°-138° C. (the slower moving spot) which was identified by analysis, PMR and IR.

Workup

  1. customThe excess phosphorous oxychloride was removed under vacuum
  2. customEvaporation of the filtrate
  3. waitleft 3.1 g of residue which

Sources & evidence

ORD record
ord-e7e0fd6827fe4e4f8db432d45338fc1d
Source dataset
uspto-grants-1986_04
Patent number
US04579848

Reaction notes

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