Ammonium Chloride → HCID 21680512, compound

HRID 1405202Notes

Reaction equation

HRID 1405202 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:5]=1)([O-])=O.[Cl-].[NH4+]>C(O)C.O.[Zn]>[C:14]1([S:11]([CH2:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[NH2:1])(=[O:12])=[O:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 51063970HCID 51063970, compound

Product 1

HCID 21680512HCID 21680512, compoundYield 82.7%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 1-nitro-3-[(phenylsulfonyl)methyl]benzene (5.15 g) in ethanol (55 mL) and water (11.4 mL) was treated with ammonium chlorid (4.99 g) at 0° C. Then zinc powder (6.10 g) was cautiously added in portions and stirred for 3 hours at RT. 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 (5.20 g) from diethyl ether furnished the pure title compound (3.80 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 (5.20 g) from diethyl ether

Sources & evidence

ORD record
ord-494035a8f7414da1b3408f4f9832c424
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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