Ammonium Chloride → HCID 58474587, compound

HRID 1400864Notes

Reaction equation

HRID 1400864 reaction equation
[F:1][C:2]1[CH:30]=[C:29]([N+:31]([O-])=O)[CH:28]=[CH:27][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[CH:26]=[CH:25][C:17]([CH2:18][N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.O.[Fe]>[NH2:31][C:29]1[CH:28]=[CH:27][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[CH:26]=[CH:25][C:17]([CH2:18][N:19]5[CH2:23][CH2:22][CH2:21][C:20]5=[O:24])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:30]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 58474806HCID 58474806, compound

Product 1

HCID 58474587HCID 58474587, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Conditions

Temperature
80 °C

Procedure

The reaction mixture consisting of the nitro compound 203 (580 mg, 1.25 mmol), iron powder (594 mg, 10.64 mmol), and ammonium chloride (57.6 mg, 1.076 mmol) in EtOH/water mixture (16 mL/8 mL) was stirred for 2 hr at 80° C. The reaction mixture was filtered while hot. The filtrate was concentrated to give title compound 204 (542 mg, 100% yield) as a brown solid. MS: 434 (MH)+.

Workup

  1. filtrationThe reaction mixture was filtered while hot
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-a9ef2917ee0e445bba909f110579a372
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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