Epichlorohydrin → 2-(2-Hydroxy-3-chloropropyl)thio-5-chloropyrimidine

HRID 905215

Reaction equation

HRID 905215 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.C(N(CC)CC)C.[CH2:16]([CH:18]1[O:20][CH2:19]1)[Cl:17]>ClCCl>[OH:20][CH:18]([CH2:16][Cl:17])[CH2:19][S:8][C:5]1[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=1

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 8471TriethylamineHCID 71403455-Chloro-2(1H)-pyrimidinethione

Product 1

HCID 204757112-(2-Hydroxy-3-chloropropyl)thio-5-chloropyrimidineYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloropyrimidine-2-thione (14 mmol) and triethylamine (14 mmol) was stirred together in dichloromethane (30 ml) for 5 min before epichlorohydrin (15 mmol) was added. The mixture was stirred at room temperature for 3 h, the solvent evaporated, the residue triturated with water, the insoluble material extracted with chloroform, the dried (MgSO4) chloroform solution evaporated and the residue crystallized from chloroform:pet. ether; yield 30%, m.p. 99° C. 1H NMR (acetone-d6): δ3.3-3.8 (2CH2, m) 3.9-4.4 (CH, m), 4.6-4.7 (OH), 8.59 (H-4, H-6).

Workup

  1. additionwas added
  2. customthe solvent evaporated
  3. customthe residue triturated with water
  4. extractionthe insoluble material extracted with chloroform
  5. dry with materialthe dried (MgSO4) chloroform solution
  6. customevaporated
  7. customthe residue crystallized from chloroform

Sources & evidence

ORD record
ord-009ebf054bff4e08ae8000ee73efa464
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Linked notes

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