Triethylamine → HCID 18551366, compound

HRID 1266472Notes

Reaction equation

HRID 1266472 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[C:12]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([OH:16])=O)([O-:10])=[O:9].ClC(OCC(C)C)=O.[F:36][C:37]1[CH:42]=[CH:41][C:40]([CH:43]([NH2:45])[CH3:44])=[CH:39][CH:38]=1>ClCCl>[N+:8]([C:11]1[C:12]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH:45][CH:43]([C:40]1[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=1)[CH3:44])=[O:16])([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 1230631-(4-Fluorophenyl)ethylamineHCID 222726693-Nitro-2-(phenylmethoxy)benzoic acid

Product 1

HCID 18551366HCID 18551366, compoundYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2.4 g (0.011 mol) of triethylamine are added at −10° C. to a solution of 3 g (0.011 mol) of 3-nitro-2-benzyloxybenzoic acid in 40 ml of dichloromethane. After the mixture has been stirred for 5 minutes, 2.8 g (0.011 mol) of isobutyl chloroformate are added dropwise at −10° C., and the mixture is stirred for a further 30 minutes. A solution of 1.53 g (0.011 mol) of 1-(4-fluorophenyl)-ethylamine in 10 ml of dichloromethane is added at −10° C., and stirring is continued for 12 hours without further cooling. The mixture is treated with sodium halogen carbonate solution, and the organic phase is separated off, washed with water and dried over sodium sulphate. After the solvent has been distilled off, 2.5 g (56% of theory) of 3-nitro-2-benzyloxy-N-[1-(4-fluorophenyl)-ethyl)-benzamide are obtained as an oil.

Workup

  1. stirringthe mixture is stirred for a further 30 minutes
  2. stirringstirring
  3. waitis continued for 12 hours without further cooling
  4. customthe organic phase is separated off
  5. washwashed with water
  6. dry with materialdried over sodium sulphate
  7. distillationAfter the solvent has been distilled off

Sources & evidence

ORD record
ord-fc2c3f0f05aa41cd9f666d1e999b3973
Source dataset
uspto-grants-2003_04
Patent number
US06548549B1

Reaction notes

Loading…