Acetic Acid → N-(4-Sulfanylphenyl)benzamide

HRID 1436843Notes

Reaction equation

HRID 1436843 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]12S[CH:12]1[CH:13]1[S:18][C:14]1(O)[CH:15]=[CH:16]2.CC(O)=O>C(Cl)Cl.[Zn]>[SH:18][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 7412Benzoyl chlorideHCID 86610051HCID 86610051, compound

Product 1

HCID 15465270N-(4-Sulfanylphenyl)benzamide

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

Benzoyl chloride (5.14 mL, 44.28 mL) was added dropwise to a mixture of 4-aminophenol disulfide (5.0 g, 20.13 mmol) and TEA (7.01 mL, 50.3 mmol) in 60 mL DCM at 0° C. The reaction was allowed to stir overnight. The resulting precipitate was collected by filtration. The solid was washed with MeOH and water and then dried. The solid was combined with 200 mL of concentrated HOAc, and 5.0 equiv of zinc powder was added. The reaction was monitored by LCMS. When the reaction was complete, the acetic acid solution was concentrated to approximately 20 mL in volume. The crude mixture was then extracted with water and EtOAc. The organic layer was dried with MgSO4 then concentrated. MS: 228 [M+H]+; 1H NMR (DMSO-d6): 10.23 (s, 1H), 7.94 (d, 2H), 7.81 (d, 2H), 7.56 (m, 3H), 7.28 (d, 2H), 5.31 (s, 1H).

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washThe solid was washed with MeOH and water
  3. customdried
  4. additionwas added
  5. concentrationthe acetic acid solution was concentrated to approximately 20 mL in volume
  6. extractionThe crude mixture was then extracted with water and EtOAc
  7. dry with materialThe organic layer was dried with MgSO4
  8. concentrationthen concentrated

Sources & evidence

ORD record
ord-bbf164d25f6a438494f6670a622456b5
Source dataset
uspto-grants-2009_11
Patent number
US07619083B2

Reaction notes

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