Chloroacetyl chloride → HCID 23458343, compound

HRID 903965Notes

Reaction equation

HRID 903965 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH:5]([OH:23])[CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15].[OH-].[Na+].[Cl:26][CH2:27][C:28](Cl)=[O:29]>O.C(Cl)Cl>[Cl:26][CH2:27][C:28]([N:3]([CH2:4][CH:5]([OH:23])[CH:6]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N+:14]([O-:16])=[O:15])[CH3:2])=[O:29]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 23458452HCID 23458452, compound

Product 1

HCID 23458343HCID 23458343, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 55 g of N-methyl-2-hydroxy-3-phenyl-3-(2-nitro-phenoxy)-propylamine hydrochloride dissolved in 770 ml of distilled water there was added at room temperature 185 ml of 2 N NaOH and 200 ml of CH2Cl2. At 0° C., slow dropwise addition was made to the mixture of 16.7 ml of chloroacetyl chloride dissolved in 350 ml of anhydrous CH2Cl2. The solution was stirred at room temperature for 3 hours. The organic phase was separated and washed with an aqueous solution of bicarbonate, then with a saturated solution of NaCl, then dried and evaporated to dryness. There was obtained 60 g (Yield 97%) of N-chloroacetyl-N-methyl-3-phenyl-2-hydroxy-3-(2-nitro-phenoxy)-propylamine.

Workup

  1. additionAt 0° C., slow dropwise addition
  2. customThe organic phase was separated
  3. washwashed with an aqueous solution of bicarbonate
  4. dry with materialwith a saturated solution of NaCl, then dried
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-f6913903d5d14269a4cc09baa9203b5d
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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