2,3-Dichlorobenzenethiol → HCID 46932330, compound

HRID 1192071Notes

Reaction equation

HRID 1192071 reaction equation
[Na].[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[SH:10].Cl[C:12]1[S:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]>C(O)C.O>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[S:10][C:12]1[S:16][C:15]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:14][C:13]=1[N+:22]([O-:24])=[O:23]

Participants

6

Reactant 3

HCID 1402022,3-DichlorobenzenethiolHCID 5360545SodiumHCID 56763846HCID 56763846, compound

Product 1

HCID 46932330HCID 46932330, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Sodium metal (0.126 g, 5.5 mmol) was dissolved in absolute ethanol (10 mL) and to the resulting solution was added 2,3-dichlorobenzenethiol (0.895 g, 5 mmol). Ethyl 5-chloro-4-nitrothiophene-2-carboxylate (1.18 g, 5 mmol) was added and the reaction mixture was stirred for 1 hour at ambient temperature and was allowed to stand overnight. After this time, the mixture was diluted with water (30 mL) and the resulting precipitate was collected by filtration and dried in vacuo at 40° C. for 1 hour. Initial analysis showed some minor impurities so the crude material was stirred in absolute ethanol (10 mL) for 30 min, collected by filtration and dried in vacuo at 40° C. for 1 hour to afford the title product as a white solid (0.67 g, 35% yield). 1H NMR (CDCl3) δ: 8.18 (1H, s), 7.71 (2H, m), 7.31 (1H, m), 4.31 (2H, q, J=7.11 Hz), 1.33 (3H, t, J=7.11 Hz).

Workup

  1. waitto stand overnight
  2. filtrationthe resulting precipitate was collected by filtration
  3. customdried in vacuo at 40° C. for 1 hour
  4. stirringwas stirred in absolute ethanol (10 mL) for 30 min
  5. filtrationcollected by filtration
  6. customdried in vacuo at 40° C. for 1 hour

Sources & evidence

ORD record
ord-54a40c3c8bee49b89089f6a595ccb50a
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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