Chloroacetic Acid → HCID 18625226, compound

HRID 1859378Notes

Reaction equation

HRID 1859378 reaction equation
[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]([NH:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=1)=[S:7])[CH2:2][CH2:3][CH3:4].[OH-].[Na+].Cl[CH2:26]C(O)=O>O>[CH2:1]([N:5]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1[S:7][CH:26]=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[N:8]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 14798Sodium HydroxideHCID 18822972HCID 18822972, compound2×

Product 1

HCID 18625226HCID 18625226, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 114.95 g (356.5 mmol) of N,N-di-n-butyl-N′-(3-methoxybenzoyl)thiourea (compound 1-24), 31.37 g (784.2 mmol) of sodium hydroxide, and 350 ml of water was prepared, to which was added 40.42 g (427.8 mmol) of chloroacetic acid. The mixture was stirred and heated on a steam bath for 23 hrs, then cooled. The mixture was extracted with methylene chloride, and the extracts were washed with water, dried over magnesium sulfate, and concentrated. The oily residue began to crystallize on standing. The yield of thiazole was 100.8 g and was used without further purification.

Workup

  1. customwas prepared, to which
  2. temperatureheated on a steam bath for 23 hrs
  3. temperaturecooled
  4. extractionThe mixture was extracted with methylene chloride
  5. washthe extracts were washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customto crystallize on standing
  9. customwas used without further purification

Sources & evidence

ORD record
ord-45bf06e15d644313a0a134eda93238f9
Source dataset
uspto-grants-2003_03
Patent number
US06528223B1

Reaction notes

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