1-{5-[(2,3-Dichlorophenyl)sulfanyl]-4-nitrothiophen-2-yl}ethan-1-one → HCID 46932142, compound

HRID 1192045Notes

Reaction equation

HRID 1192045 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12]1[S:16][C:15]([C:17](=[O:19])[CH3:18])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21]>CO>[Cl:3][C:4]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:5]=1[S:11][C:12]1[S:16][C:15]([CH:17]([OH:19])[CH3:18])=[CH:14][C:13]=1[N+:20]([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 28199931-{5-[(2,3-Dichlorophenyl)sulfanyl]-4-nitrothiophen-2-yl}ethan-1-oneHCID 4311764Sodium borohydride

Product 1

HCID 46932142HCID 46932142, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (54 mg, 1.44 mmol) was added to a suspension of 1-[5-(2,3-dichlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone (0.5 g, 1.44 mmol) in methanol (10 mL) and the resulting mixture was stirred at ambient temperature. After 90 minutes, TLC showed no starting material remaining so the reaction was quenched by addition of water (20 mL). The resulting precipitate was collected by filtration and dissolved in dichloromethane (50 mL). The organic solution was dried over magnesium sulfate (MgSO4), filtered and the solvent removed to give a yellow solid. The crude solid was re-crystallized from methanol to afford the title product as a yellow solid (0.164 g, 33% yield). 1H NMR (300 MHz, CDCl3) δ: 7.65 (2H, m), 7.40 (1H, m), 7.33 (1H, t), 4.94 (1H, q), 1.99 (1H, d, J=4.74 Hz), 1.51 (3H, d, J=6.48 Hz).

Workup

  1. customwas quenched by addition of water (20 mL)
  2. filtrationThe resulting precipitate was collected by filtration
  3. dissolutiondissolved in dichloromethane (50 mL)
  4. dry with materialThe organic solution was dried over magnesium sulfate (MgSO4)
  5. filtrationfiltered
  6. customthe solvent removed
  7. customto give a yellow solid
  8. customThe crude solid was re-crystallized from methanol

Sources & evidence

ORD record
ord-1f107bdfff6b474cb0ab95fe0f678475
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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