Methanol → 1-[5-(2-Chlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone

HRID 1192029Notes

Reaction equation

HRID 1192029 reaction equation
C[O-].[Na+].CO.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[SH:13].Cl[C:15]1[S:19][C:18]([C:20](=[O:22])[CH3:21])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24]>>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[S:13][C:15]1[S:19][C:18]([C:20](=[O:22])[CH3:21])=[CH:17][C:16]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 4

HCID 887MethanolHCID 80599o-ChlorothiophenolHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 469318591-[5-(2-Chlorophenylsulfanyl)-4-nitro-2-thienyl]ethanoneYield 52.6%

Procedure

To a 0.1 M stock solution of sodium methoxide in anhydrous methanol (11 mL, 1.1 mmol) was added the 2-chlorobenzenethiol (0.144 g, 1 mmol) and the resulting mixture stirred at ambient temperature for 15 minutes. 1-(5-Chloro-4-nitro-2-thienyl)ethanone (206 mg, 1 mmol) was added and the mixture was stirred at ambient temperature for 2 hours. After this time the reaction was quenched by the addition of water (15 mL) and the resulting precipitate was collected by filtration, washed with water (10 mL) and dried in vacuo at 40° C. overnight. The solid was then crystallized from acetonitrile to afford the title compound as a dark orange solid (165 mg, 52.6% yield). 1H NMR (300 MHz, CDCl3) δ: 8.09 (1H, s), 7.77 (1H, ddd, J=7.58, 1.58, 0.36 Hz), 7.40-7.67 (3H, m), 2.49 (3H, s).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2 hours
  2. customAfter this time the reaction was quenched by the addition of water (15 mL)
  3. filtrationthe resulting precipitate was collected by filtration
  4. washwashed with water (10 mL)
  5. customdried in vacuo at 40° C. overnight
  6. customThe solid was then crystallized from acetonitrile

Sources & evidence

ORD record
ord-2f44c476b36a489baf4fb93f31035087
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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