Ammonium Chloride → tert-Butyl {3-[6-amino-1-(3-methylbut-2-enyl)-1H-benzimidazol-2-ylsulfanyl]propyl}carbamate

HRID 1714179Notes

Reaction equation

HRID 1714179 reaction equation
[CH3:1][C:2]([CH3:29])=[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[S:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].[Cl-].[NH4+]>C(O)C.O.[Fe]>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]2[N:7]=[C:6]([S:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[N:5]([CH2:4][CH:3]=[C:2]([CH3:29])[CH3:1])[C:9]=2[CH:10]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86619700tert-butyl {3-[1-(3-methylbut-2-enyl)-6-nitro-1H-benzimidazol-2-ylsulfanyl]propyl}carbamate

Product 1

HCID 59464722tert-Butyl {3-[6-amino-1-(3-methylbut-2-enyl)-1H-benzimidazol-2-ylsulfanyl]propyl}carbamateYield 107.1%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 140 mg (0.33 mmol) of tert-butyl {3-[1-(3-methylbut-2-enyl)-6-nitro-1H-benzimidazol-2-ylsulfanyl]propyl}carbamate in 15 ml of ethanol was added dropwise to a suspension of 93 mg (1.66 mmol) of iron and 16 mg (0.30 mmol) of ammonium chloride in 1.5 ml of water and boiled at reflux for 3 hours. The catalyst was filtered off and washed with ethanol. The filtrate was concentrated under reduced pressure. The 138 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-bf785caf84134e6c8724c8b7052e787f
Source dataset
uspto-grants-2010_09
Patent number
US07795445B2

Reaction notes

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