Ammonia → 2-[2-(4-Carbamoylmethyl-2-chlorophenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol

HRID 1682711Notes

Reaction equation

HRID 1682711 reaction equation
C[O:2][C:3]([CH2:5][C:6]1[CH:26]=[CH:25][C:9]([O:10][CH2:11][CH:12]([NH:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[OH:17])[CH3:13])=[C:8]([Cl:27])[CH:7]=1)=O.[NH3:28]>CO>[C:3]([CH2:5][C:6]1[CH:26]=[CH:25][C:9]([O:10][CH2:11][CH:12]([NH:14][CH2:15][CH:16]([C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[CH:19]=2)[OH:17])[CH3:13])=[C:8]([Cl:27])[CH:7]=1)(=[O:2])[NH2:28]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 218321762-[2-(4-Methoxycarbonylmethyl-2-chlorophenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol

Product 1

HCID 571941612-[2-(4-Carbamoylmethyl-2-chlorophenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2 g of 2-[2-(4-methoxycarbonylmethyl-2-chlorophenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol (prepared as described in Example 22) dissolved in 50 ml of methanol was saturated with gaseous ammonia in a reaction vessel, whilst ice-cooling, after which the reaction vessel was tightly stoppered and allowed to stand at room temperature for one week. At the end of this time, the solvent (methanol) was removed by distillation under reduced pressure, and the residue was recrystallized from ethyl acetate, to give 0.55 g of the title compound as crystals, melting at 99°-101° C.

Workup

  1. temperaturecooling
  2. waitto stand at room temperature for one week
  3. customAt the end of this time, the solvent (methanol) was removed by distillation under reduced pressure
  4. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ad96cc2abd2b4d6883072b4dbe7c444b
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

Loading…