Ammonium Chloride → HCID 63114873, compound

HRID 1405206Notes

Reaction equation

HRID 1405206 reaction equation
[CH:1]1([S:6]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl-].[NH4+]>C(O)C.O.[Zn]>[CH:1]1([S:6]([CH2:9][C:10]2[CH:11]=[C:12]([CH:13]=[CH:14][CH:15]=2)[NH2:16])(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 70976430HCID 70976430, compound

Product 1

HCID 63114873HCID 63114873, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-[(cyclopentylsulfonyl)methyl]-3-nitrobenzene (4.9 g) in ethanol (37 mL) and water (11.1 mL) was treated with ammonium chloride (4.9 g) at 0° C. Then zinc powder (5.9 g) was cautiously added in portions and stirred for 3 hours at room temperature. Then the mixture was filtered over cellite, washed with ethanol, condensed to dryness, treated with ethyl acetate, washed with brine, dried with sodium sulfate and condensed to dryness. Crystallization of the crude product (4.5 g) from diethyl ether furnished the pure title compound (3.6 g).

Workup

  1. filtrationThen the mixture was filtered over cellite
  2. washwashed with ethanol, condensed to dryness
  3. additiontreated with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried with sodium sulfate and condensed to dryness
  6. customCrystallization of the crude product (4.5 g) from diethyl ether

Sources & evidence

ORD record
ord-c9e7ec0303a04693a3e794b02986979c
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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