Methanol → HCID 13478001, compound

HRID 371480Notes

Reaction equation

HRID 371480 reaction equation
Cl.Cl.C[O:4][C:5]1[CH:24]=[CH:23][C:8]([CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:7][CH:6]=1.B(Br)(Br)[Br:26].CO>C(Cl)Cl>[BrH:26].[BrH:26].[OH:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[C:11]2[CH2:15][NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 13477999HCID 13477999, compound

Product 1

HCID 13478001HCID 13478001, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 1.6 g (0.0044 mole) of 1-(4-methoxybenzyl)-2-phenylaminomethyl imidazole dihydrochloride in 100 ml of CH2Cl2 was converted to its free base by washing with aqueous NaHCO3. The CH2Cl2 was dried (K2CO3), and filtered, and the filtrate was treated with a solution of 3.3 g (0.013 mole) of BBr3 in 9 ml of CH2Cl2. After 3 hr, methanol was cautiously added and all the solvents were evaporated. The residue was recrystallized from methanol and diethyl ether to give 1-(4-hydroxybenzyl)-2-phenylaminomethyl imidazole dihydrobromide, 0.73 gm (39%), mp 198°-200°.

Workup

  1. washby washing with aqueous NaHCO3
  2. dry with materialThe CH2Cl2 was dried (K2CO3)
  3. filtrationfiltered
  4. customall the solvents were evaporated
  5. customThe residue was recrystallized from methanol and diethyl ether

Sources & evidence

ORD record
ord-495e79d04e23430db264cac6b968be9b
Source dataset
uspto-grants-1985_07
Patent number
US04532331

Reaction notes

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