Chlorosuccinimide → HCID 14154432, compound

HRID 1073517Notes

Reaction equation

HRID 1073517 reaction equation
[O:1]([C:8]1[CH:23]=[CH:22][C:11]([O:12][CH2:13][CH2:14][S:15][C:16]2[N:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:24]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:24][CH:14]([S:15][C:16]1[N:17]=[CH:18][CH:19]=[CH:20][N:21]=1)[CH2:13][O:12][C:11]1[CH:22]=[CH:23][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 133867602-{[2-(4-Phenoxyphenoxy)ethyl]sulfanyl}pyrimidine

Product 1

HCID 14154432HCID 14154432, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 2-[2-(4-phenoxyphenoxy)ethylthio]pyrimidine (324 mg, 1.0 mmol) in carbon tetrachloride (3 ml), there was added N-chlorosuccinimide (160 mg, 1.2 mmol) with stirring under ice-cooling. The reaction system was gradually elevated to room temperature, and stirring was continued overnight. The precipitate was separated by filtration, and the filtrate was concentrated. Recrystallization of the residue from cyclohexane gave 2-[1-chloro-2-(4-phenoxyphenoxy)ethylthio]pyrimidine (268 mg) as pale yellow crystals. M.P., 86.0° C.

Workup

  1. temperaturecooling
  2. customwas gradually elevated to room temperature
  3. stirringstirring
  4. customThe precipitate was separated by filtration
  5. concentrationthe filtrate was concentrated
  6. customRecrystallization of the residue from cyclohexane

Sources & evidence

ORD record
ord-bf4a00841ed4473086c8d20203e313e2
Source dataset
uspto-grants-1990_11
Patent number
US04970222

Reaction notes

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