2-Chloroacetophenone → HCID 52915361, compound

HRID 500651Notes

Reaction equation

HRID 500651 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[C:4]([NH2:9])[CH:3]=1.[CH2:10](Cl)[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=O>C1C=CC=CC=1.C(Cl)Cl>[CH2:11]([C:10]1[S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[N:9]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 107572-ChloroacetophenoneHCID 120002-Amino-4-chlorobenzenethiol

Product 1

HCID 52915361HCID 52915361, compoundYield 34.4%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask fitted with a Dean-Stark trap was charged with 4-Chloro-2-aminobenzenethiol (3.47 g, 21.7 mmol) and phenacyl chloride (3.0 mL, 22.7 mmol) in benzene (40 mL), and the mixture heated 18 h in an 80° C. oil bath. The reaction mixture was diluted with CH2Cl2, and the organics washed sequentially with aqueous Na2CO3, brine, then dried over MgSO4. The solvent was removed under reduced pressure, and the residue purified by silica gel chromatography eluting with 35-100% CH2Cl2/hexanes to provide the title compound as a white solid (1.94 g).

Workup

  1. customA round bottom flask fitted with a Dean-Stark trap
  2. washthe organics washed sequentially with aqueous Na2CO3, brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue purified by silica gel chromatography
  6. washeluting with 35-100% CH2Cl2/hexanes

Sources & evidence

ORD record
ord-44409b6491c14da3ba1c8b1b0d8c0a51
Source dataset
uspto-grants-2010_08
Patent number
US07772231B2

Reaction notes

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