Hydrazine hydrate (1:1) → 4-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole

HRID 636478Notes

Reaction equation

HRID 636478 reaction equation
[Cl:1][C:2]1[C:20]([N:21]([C:23](=[O:36])[CH2:24][N:25]2C(=O)C3=CC=CC=C3C2=O)[CH3:22])=[CH:19][CH:18]=[C:17]([Cl:37])[C:3]=1[CH2:4][O:5][C:6]1[C:14]2[N:13]=[C:12]([CH3:15])[N:11]([CH3:16])[C:10]=2[CH:9]=[CH:8][CH:7]=1.O.NN>C(O)C>[NH2:25][CH2:24][C:23]([N:21]([C:20]1[C:2]([Cl:1])=[C:3]([C:17]([Cl:37])=[CH:18][CH:19]=1)[CH2:4][O:5][C:6]1[C:14]2[N:13]=[C:12]([CH3:15])[N:11]([CH3:16])[C:10]=2[CH:9]=[CH:8][CH:7]=1)[CH3:22])=[O:36]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 154621754-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-1,2-dimethyl-1H-benzimidazole

Product 1

HCID 154621764-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazoleYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-[2,6-dichloro-3-[N-(phthalimidoacetyl)-N-methylamino]benzyloxy]-1,2-dimethyl-1H-benzimidazole (405 mg), hydrazine monohydrate (75.4 mg) and ethanol (4.0 ml) was refluxed for 30 minutes. After cooling, the resulting precipitate was filtered off, and the filtrate was concentrated in vacuo to give 4-[3-(N-glycyl-N-methylamino)-2,6-dichlorobenzyloxy]-1,2-dimethyl-1H-benzimidazole (300 mg).

Workup

  1. temperaturewas refluxed for 30 minutes
  2. temperatureAfter cooling
  3. filtrationthe resulting precipitate was filtered off
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d255e4f6443a44fb8dcfc505c9907bae
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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