Phosphorus oxychloride → HCID 14794216, compound
Reaction equation
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20](O)[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].P(Cl)(Cl)([Cl:33])=O>>[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[C:20]([Cl:33])[C:19]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:18][N:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
Procedure
Ethyl benzyloxyacetate (B) was obtained by esterifying benzyloxyacetic acid as obtained from benzyl alcohol and chloroacetic acid by a conventional Williamson synthesis. (B) (9.7 g) and 3.7 g of ethyl formate were dissolved in 25 ml of ether, and stirred in the presence of sodium for 2 hours, and ether was distilled away to obtain sodium 2-benzyloxy-2-ethoxycarbonylethylenolate (C). To this compound was added a solution as prepared by dissolving 14.2 g of 4-decyloxybenzamidine hydrochloride (synthesized from 4-decyloxycyanobenzene by a conventional method) in 80 ml of ethanol and adding 1.2 g of sodium, and the mixture was refluxed for 2 hours. The solvent was distilled away to obtained 2-(4-octyloxyphenyl)-4-hydroxy-5-benzyloxypyrimidine (D). (D) (2 g) together with phosphorus oxychloride was refluxed for 3 hours to obtain 2-(4-octyloxyphenyl)-4-chloro-5-benzyloxypyrimidine (E).
Sources & evidence
- ORD record
- ord-d0f03efb6490439badb3631545a165ab
- Source dataset
- uspto-grants-1989_10
- Patent number
- US04874542
Reaction notes
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