Ammonium Chloride → HCID 57796670, compound

HRID 2099899Notes

Reaction equation

HRID 2099899 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][CH2:20][CH:19]2[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:24][CH:18]12.[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[CH2:21][CH2:20][CH:19]4[CH2:22][N:23]([C:25]([O:27][C:28]([CH3:30])([CH3:31])[CH3:29])=[O:26])[CH2:24][CH:18]34)[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 57796672HCID 57796672, compound

Product 1

HCID 57796670HCID 57796670, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 49 mg (0.11 mmol) of tert-butyl 1-[1-(3-methylbut-2-enyl)-6-nitro-1H-benzimidazol-2-yl]hexahydropyrrolo[3,4-b]pyrrole-5-carboxylate in 7.5 ml of ethanol was added dropwise to a suspension of 62 mg (1.11 mmol) of iron and 11 mg (0.20 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 43 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-97b06ac9989f47448edb5d1ea4d7dc24
Source dataset
uspto-grants-2009_08
Patent number
US07569700B2

Reaction notes

Loading…