Chloroacetyl chloride → HCID 23458451, compound

HRID 1679995Notes

Reaction equation

HRID 1679995 reaction equation
[C:1]1([CH:7]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])[CH:8]([OH:11])[CH2:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl.O>[Cl:23][CH2:24][C:25]([NH:10][CH2:9][CH:8]([OH:11])[CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[O:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[O:19][CH3:20])=[O:26]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 15572608HCID 15572608, compound

Product 1

HCID 23458451HCID 23458451, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2.73 g of 3-phenyl-2-hydroxy-3-(2-methoxy-phenoxy)-propylamine in 50 ml of methylene chloride and 0.56 g of NaOH in 15 ml of water was stirred at 0° C. Under vigorous stirring dropwise addition was made to the mixture over 30 minutes, again at 0° C., of 1.58 g of chloroacetyl chloride in 2 ml of methylene chloride. After the addition, the stirring was continued at 0° C. for 30 minutes. The layers were separated and the aqueous phase extracted with CH2Cl2. The organic extracts were combined and washed with water, dried over Na2SO4 and evaporated to dryness. There was obtained 3.49 g of N-chloroacetyl-2-hydroxy-3-phenyl-3-(2-methoxy-phenoxy)propylamine (oil). Yield 100%.

Workup

  1. stirringUnder vigorous stirring dropwise
  2. additionaddition
  3. additionAfter the addition
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with CH2Cl2
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. customevaporated to dryness

Sources & evidence

ORD record
ord-5bb4036768a1473d90baa3b808fcb95e
Source dataset
uspto-grants-1981_06
Patent number
US04271160

Reaction notes

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