Water → HCID 178467471, compound

HRID 1380845Notes

Reaction equation

HRID 1380845 reaction equation
S(Cl)([Cl:4])(=O)=O.[CH2:6]([O:8][C:9]1[N:14]=[C:13]([CH2:15][Cl:16])[CH:12]=[C:11]([OH:17])[N:10]=1)[CH3:7].O.[OH-].[Na+]>C(Cl)Cl>[CH2:6]([O:8][C:9]1[N:14]=[C:13]([CH2:15][Cl:16])[C:12]([Cl:4])=[C:11]([OH:17])[N:10]=1)[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24648Sulfuryl chlorideHCID 178467470HCID 178467470, compound

Product 1

HCID 178467471HCID 178467471, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.8 ml (0.035 mol) of sulphuryl chloride are added dropwise to a solution of 6 g (0.032 mol) of 2-ethoxy-4-chloromethyl-6-hydroxy-pyrimidine in 90 ml of methylene chloride and the mixture is subsequently stirred at room temperature for 4 hours. The mixture is then treated with 100 ml of water and adjusted to pH 7 with 30% sodium hydroxide solution. The organic phase is separated and the combined organic phases are extracted with water, dried over anhydrous sodium sulphate and evaporated. There is obtained crystalline 2-ethoxy-5-chloro-4-chloromethyl-6-hydroxy-pyrimidine, 1H-NMR (CDCl3): 1.45 (t, OCH2CH3), 4.54 (q, OCH2CH3), 4.54 (s, CH2Cl), 9.80 (broad signal, OH).

Workup

  1. customThe organic phase is separated
  2. extractionthe combined organic phases are extracted with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated

Sources & evidence

ORD record
ord-a6758658e58b4523ada9af1e3b2b024d
Source dataset
uspto-grants-1986_04
Patent number
US04584295

Reaction notes

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