Ammonium Chloride → HCID 67040595, compound

HRID 883937Notes

Reaction equation

HRID 883937 reaction equation
[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[N+:31]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>O.C(O)C.C(OCC)(=O)C.[Fe]>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([C:21](=[O:30])[NH:22][C:23]3[CH:28]=[CH:27][C:26]([Br:29])=[CH:25][CH:24]=3)=[CH:17][C:16]=2[NH2:31])=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 2

HCID 25517Ammonium ChlorideHCID 67040851HCID 67040851, compound

Product 1

HCID 67040595HCID 67040595, compoundYield 95.4%

Reagents, catalysts & solvents 4

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of the product of Example 51B (1.198 g, 2.20 mmol), iron powder (756 mg, 13.53 mmol), and ammonium chloride (771 mg, 14.41 mmol) in water (15 mL) and ethanol (30 mL) was heated at 90° for 1 hour. The reaction was cooled to room temperature. The mixture was diluted with ethyl acetate (200 mL) and washed with water (2×50 mL) and brine (50 mL). The organic phase was dried over sodium sulfate, filtered, and concentrated under vacuum to provide the title compound as a light yellow solid (1.08 g, 95%).

Workup

  1. temperaturewas heated at 90° for 1 hour
  2. washwashed with water (2×50 mL) and brine (50 mL)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f6facde598e0493880b7aed7b87fb916
Source dataset
uspto-grants-2012_08
Patent number
US08236950B2

Reaction notes

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