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

HRID 2396403Notes

Reaction equation

HRID 2396403 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-2199beb11d7f418cb85e9ee5a0f469e2
Source dataset
uspto-grants-1996_02
Patent number
US05491241

Reaction notes

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