2-Chloroethanol → HCID 15574554, compound

HRID 1658123Notes

Reaction equation

HRID 1658123 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:9]=[CH:10][C:11]3[C:17](=[O:18])[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15][NH:14][C:12]=3[N:13]=2)[CH2:4][CH2:3]1.[H-].[Na+].[CH2:26](Cl)[CH2:27][OH:28]>CN(C)C=O>[OH:28][CH2:27][CH2:26][N:14]1[C:12]2[N:13]=[C:8]([N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[N:9]=[CH:10][C:11]=2[C:17](=[O:18])[C:16]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:15]1

Participants

5

Reactant 3

HCID 342-ChloroethanolHCID 24758Sodium hydrideHCID 15574553HCID 15574553, compound

Product 1

HCID 15574554HCID 15574554, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture containing 5.0 g of ethyl 5,8-dihydro-2-(4-methyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate, 70 ml of dimethylformamide, 0.90 g of 50% sodium hydride, and 3.8 g of ethylene chlorohydrin was heated at 100°C for one hour. Dimethylformamide was distilled off in vacuo, and the residue taken up in chloroform. The chloroform solution was washed with water, dried over anhydrous magnesium sulfate, and the solvent distilled off. The resulting solid was recrystallized from ethanol to yield 4.6 g of the product, m.p. 197° - 199°C.

Workup

  1. distillationDimethylformamide was distilled off in vacuo
  2. washThe chloroform solution was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent distilled off
  5. customThe resulting solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-bf386cbe9b5a4c6797a2efd279856d8c
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

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