4-Methyl-5-(2-hydroxyethyl)thiazole → 103871-46-1

HRID 1684641Notes

Reaction equation

HRID 1684641 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[S:8][CH:7]=[N:6][C:5]=1[CH3:9].[Br:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13]>C(O)C>[Br-:10].[CH2:15]([O:14][C:12]([CH2:11][N+:6]1[C:5]([CH3:9])=[C:4]([CH2:3][CH2:2][OH:1])[S:8][CH:7]=1)=[O:13])[CH3:16]

Participants

4

Reactant 2

HCID 11364-Methyl-5-(2-hydroxyethyl)thiazoleHCID 7748Ethyl bromoacetate

Product 1

HCID 10935796103871-46-1Yield 71.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5-(2-hydroxyethyl)-4-methylthiazole (306 g) and ethyl bromoacetate (356.2 g) in ethanol (1 L) was heated to reflux. After two hours, the ethanol was removed by distillation and the residue treated with isopropanol (1.5 L). The resulting solution was cooled to about 0° C., causing crystallization of compound 1. After three hours, the crystalline material was separated from the mother liquor. Additional crystals were obtained by prolonged cooling of the mother liquor at 0° C. Combination of the crystalline material gave 474.3 g of compound 1. Melting point 96°-98° C.

Workup

  1. customthe ethanol was removed by distillation
  2. additionthe residue treated with isopropanol (1.5 L)
  3. customcrystallization of compound 1
  4. waitAfter three hours
  5. customthe crystalline material was separated from the mother liquor
  6. customAdditional crystals were obtained
  7. temperatureby prolonged cooling of the mother liquor at 0° C

Sources & evidence

ORD record
ord-ec0ef138885940ce878ddf63f1ebc86d
Source dataset
uspto-grants-1997_06
Patent number
US05641798

Reaction notes

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