Acetonitrile → HCID 178465588, compound

HRID 1455955Notes

Reaction equation

HRID 1455955 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:10]=1[CH2:11][NH:12]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Al](C)C.[C:23](#[N:25])[CH3:24].ClCCl>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:10]=1[CH2:11][NH:12][C:23](=[NH:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 6344DichloromethaneHCID 16682925TrimethylaluminumHCID 86753383HCID 86753383, compound

Product 1

HCID 178465588HCID 178465588, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a mixture of 2-benzyloxy-5-bromobenzylamino hydrochloride (10 g) in toluene (75 ml) at 4° C. was added a solution of trimethylaluminium in toluene (2M, 15.2 ml). The mixture was stirred at ambient temperature for 2 hours, acetonitrile (6.5 ml) added and the mixture heated at 80° C. for 18 hours. The mixture was cooled and poured onto a slurry of silica gel (300 g), and dichloromethane. The solvent was filtered off and the product eluted from the silica gel with methanol to give N1 -[2-benzyloxy-5-bromobenzyl]acetamidine (5.51 g).

Workup

  1. temperaturethe mixture heated at 80° C. for 18 hours
  2. temperatureThe mixture was cooled
  3. filtrationThe solvent was filtered off
  4. washthe product eluted from the silica gel with methanol

Sources & evidence

ORD record
ord-e32bb3785ba845b2bafe19cd2cff8b37
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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