Ethanolamine → 4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio(N-beta-hydroxyethyl)acetamide

HRID 1449030Notes

Reaction equation

HRID 1449030 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=2[CH3:16])[N:5]=[C:4]([S:17][CH2:18][C:19]([OH:21])=O)[N:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[CH2:35]([CH2:37][NH2:38])[OH:36]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=2[CH3:16])[N:5]=[C:4]([S:17][CH2:18][C:19]([NH:38][CH2:37][CH2:35][OH:36])=[O:21])[N:3]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 5694[4-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio]acetic acidHCID 8471TriethylamineHCID 10928Ethyl chloroformate

Product 1

HCID 688514-Chloro-6-(2,3-xylidino)-2-pyrimidinylthio(N-beta-hydroxyethyl)acetamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To the solution of [4-chloro-6-(2,3-xylidino)-2-pyrimidinyl-thio]-acetic acid (85 g.), triethylamine (45 ml.), in anhydrous chloroform (750 ml.), cooled to -5° C., 35 ml. of ethyl chlorocarbonate and then 22 ml. of ethanolamine were added with stirring while the temperature was kept below +10° C. The reaction mixture was washed with water (350 ml.), and dried over sodium sulphate and the solvent was removed under reduced pressure. The residue was washed with benzene (500 ml.) and crystallised several times from acetone. 55 g. of [4-chloro-6-(2,3-xylidino)-2-pyrimidinyl-thio]-(N-β-hydroxyethyl)-acetamide were obtained, identical with the compound prepared as in Example 1.

Workup

  1. customwas kept below +10° C
  2. washThe reaction mixture was washed with water (350 ml.)
  3. dry with materialdried over sodium sulphate
  4. customthe solvent was removed under reduced pressure
  5. washThe residue was washed with benzene (500 ml.)
  6. customcrystallised several times from acetone

Sources & evidence

ORD record
ord-f69fcb085a4b4fbf81a52f254f9a9fd0
Source dataset
uspto-grants-1980_02
Patent number
US04188484

Reaction notes

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