4-Chlorophenol → 2-(4-Chlorophenoxymethyl)thio-5-chloropyrimidine

HRID 905222Notes

Reaction equation

HRID 905222 reaction equation
I[CH2:2][S:3][C:4]1[N:9]=[CH:8][C:7]([Cl:10])=[CH:6][N:5]=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1.CC[O-].[Na+]>C(O)C>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:2][S:3][C:4]2[N:9]=[CH:8][C:7]([Cl:10])=[CH:6][N:5]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 46844-ChlorophenolHCID 2723922Sodium ethoxideHCID 134351362-(Iodomethyl)thio-5-chloropyrimidine

Product 1

HCID 204757412-(4-Chlorophenoxymethyl)thio-5-chloropyrimidineYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(Iodomethyl)thio-5-chloropyrimidine was added to a solution of p-chlorophenol (5.5 mmol) and 0.138 M NaOEt in ethanol (40 ml) and the mixture stirred at room temperature overnight. The solvent was distilled off and the mixture worked up as above; yield 64%.

Workup

  1. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-e01055291f9f47b9b210f83ac20327af
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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