Tetrahydrofuran → 4-benzyloxy-1-methyl-2-methylamino-1H-benzimidazole

HRID 636501Notes

Reaction equation

HRID 636501 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([NH2:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][N:19]=C=S.O1CCC[CH2:23]1>>[CH2:1]([O:8][C:9]1[C:10]2[N:17]=[C:13]([NH:19][CH3:18])[N:12]([CH3:23])[C:11]=2[CH:14]=[CH:15][CH:16]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 11167Methyl isothiocyanateHCID 104895412-amino-3-benzyloxy-N-methylaniline

Product 1

HCID 106594804-benzyloxy-1-methyl-2-methylamino-1H-benzimidazole

Procedure

To a mixture of 3-benzyloxy-2-amino-N-methylaniline (200 mg) and methyl isothiocyanate (70.5 mg) was added tetrahydrofuran (2 ml) at ambient temperature, and the mixture was stirred for 2 days. The solvent was removed in vacuo, and the residue was dissolved in acetonitrile (2 ml). Methyl iodide (149 mg) was added thereto under ice-cooling, the mixture was stirred for 5 hours. The reaction mixture was concentrated in vacuo, and the residue was crystallized with ethyl acetate and recrystallized with acetonitrile to give 4-benzyloxy-1-methyl-2-methylamino-1H-benzimidazole (148 mg).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in acetonitrile (2 ml)
  3. additionMethyl iodide (149 mg) was added
  4. temperatureunder ice-cooling
  5. stirringthe mixture was stirred for 5 hours
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. customthe residue was crystallized with ethyl acetate
  8. customrecrystallized with acetonitrile

Sources & evidence

ORD record
ord-97913a0295204b1391dff25414d11814
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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