Thionyl Chloride → HCID 15574555, compound

HRID 1658124Notes

Reaction equation

HRID 1658124 reaction equation
O[CH2:2][CH2:3][N:4]1[C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[N:12]=[CH:13][C:8]=2[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]1.S(Cl)([Cl:29])=O>C(Cl)(Cl)Cl>[Cl:29][CH2:2][CH2:3][N:4]1[C:9]2[N:10]=[C:11]([N:14]3[CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[N:12]=[CH:13][C:8]=2[C:7](=[O:21])[C:6]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:5]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15574554HCID 15574554, compound

Product 1

HCID 15574555HCID 15574555, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 8.0 g of ethyl 5,8-dihydro-8-(2-hydroxyethyl)-2-(4-methyl-1-piperazinyl)-5-oxopyrido[2,3-d]pyrimidine-6-carboxylate in 80 ml of chloroform was added with stirring 6 ml of thionyl chloride, the resulting mixture was allowed to react at room temperature for 30 minutes and then heated to refux for 2 hours. After removal of the solvent and an excess of the reagent, the residue was taken up in chloroform. The chloroform solution was washed with water, dried and the solvent distilled off. The solid obtained was recrystallized from ethyl acetate to give 6.9 g of the product, m.p. 154° - 155°C.

Workup

  1. customto react at room temperature for 30 minutes
  2. temperatureheated
  3. customAfter removal of the solvent
  4. washThe chloroform solution was washed with water
  5. customdried
  6. distillationthe solvent distilled off
  7. customThe solid obtained
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e1df97b2ca974273878d72d90de58b4e
Source dataset
uspto-grants-1976_06
Patent number
US03962443

Reaction notes

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