Chloroacetyl chloride → HCID 21710587, compound

HRID 651037Notes

Reaction equation

HRID 651037 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].[Cl:20][CH2:21][C:22](Cl)=[O:23]>ClCCl>[CH2:1]([N:8]([CH2:9][C:10]1[S:11][CH:12]=[CH:13][N:14]=1)[C:22](=[O:23])[CH2:21][Cl:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 47776191-phenyl-N-(1,3-thiazol-2-ylmethyl)methanamine

Product 1

HCID 21710587HCID 21710587, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of N-benzyl-N-2-thiazolylmethylamine (204 mg, 1.0 mmol) in 5 mL of dichloromethane was cooled to 0° C. The solution was treated with 5 mL of saturated, aqueous NaHCO3 followed by the addition of chloroacetyl chloride (0.088 mL, 1.1 mmol). The biphasic mixture was stirred vigorously for 1 hour and poured into a separatory funnel. The layers were separated and the aqueous layer extracted with an additional 5 mL portion of dichloromethane. The combined organic phases were dried (Na2SO4), filtered, and concentrated to provide the title compound which was used in the next step without further purification.

Workup

  1. additionpoured into a separatory funnel
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with an additional 5 mL portion of dichloromethane
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-982abc046e304a33995aa4c6cb38b476
Source dataset
uspto-grants-2001_08
Patent number
US06277871B1

Reaction notes

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