Ammonium Chloride → HCID 18973878, compound

HRID 2395049Notes

Reaction equation

HRID 2395049 reaction equation
[Cl-].[NH4+:2].C[Al](C)C.[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]([CH3:24])[C:22]#[N:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:7]([O:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH:21]([CH3:24])[C:22]([NH2:2])=[NH:23])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 15075535HCID 15075535, compoundHCID 16682925Trimethylaluminum

Product 1

HCID 18973878HCID 18973878, compoundYield 149.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent3×HCID 6212ChloroformSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of ammonium chloride (4.49 g) in toluene (25.5 ml) at 5° C. was added trimethylaluminium (2M solution in toluene, 42 ml. The mixture was stirred for 2 hours. 2-(2-benzyloxyphenyl)-propionitrile (10 g) in toluene (50 ml) was added and the mixture heated at 80° C. for 18 hours. The cooled mixture was poured into a slurry of silica gel in chloroform, stirred for 5 minutes and filtered. The silica gel was washed with methanol and the combined organic solutions evaporated to give 2-(2-benzyloxyphenyl)propionamidine (16 g).

Workup

  1. stirringstirred for 5 minutes
  2. filtrationfiltered
  3. washThe silica gel was washed with methanol
  4. customthe combined organic solutions evaporated

Sources & evidence

ORD record
ord-2d904e05cf9a49be976b954b6435749a
Source dataset
uspto-grants-1998_09
Patent number
US05811459

Reaction notes

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