Ammonium Chloride → HCID 57796669, compound

HRID 2099901Notes

Reaction equation

HRID 2099901 reaction equation
[CH3:1][C:2]([CH3:32])=[CH:3][CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([N+:14]([O-])=O)[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[N:17]1[CH2:21][CH:20]2[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH:19]2[CH2:18]1.[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([N:17]3[CH2:18][CH:19]4[CH2:24][N:23]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:22][CH:20]4[CH2:21]3)[N:5]([CH2:4][CH:3]=[C:2]([CH3:32])[CH3:1])[C:9]=2[CH:10]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 57796674HCID 57796674, compound

Product 1

HCID 57796669HCID 57796669, compoundYield 85%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 44 mg (0.10 mmol of tert-butyl 5-[1-(3-methylbut-2-enyl)-6-nitro-1H-benzimidazol-2-yl]hexahydropyrrolo[3,4-c]pyrrole-2-carboxylate in 7.5 ml of ethanol was added dropwise to a suspension of 56 mg (1.00 mmol) of iron and 10 mg (0.18 mmol) of ammonium chloride in 0.75 ml of water, and the mixture was boiled at reflux for 3 hours. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated under reduced pressure. The 35 mg of the desired product thus obtained were used in the next stage without further purification.

Workup

  1. temperatureat reflux for 3 hours
  2. filtrationThe catalyst was filtered off
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c2c5ffb2d9b248d4841f3b69e54f77e8
Source dataset
uspto-grants-2009_08
Patent number
US07569700B2

Reaction notes

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