Dimethylformamide → Ethyl 2-[2-nitro-3-(2-chlorophenylthio)phenyl]acetate

HRID 2418334Notes

Reaction equation

HRID 2418334 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[N+:9]([C:12]1[C:17](Cl)=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:11])=[O:10].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[N+:9]([C:12]1[C:17]([S:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 80599o-ChlorothiophenolHCID 20446267Ethyl 2-(3-chloro-2-nitrophenyl)acetate

Product 1

HCID 20446149Ethyl 2-[2-nitro-3-(2-chlorophenylthio)phenyl]acetate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 2-chlorobenzenethiol (8.0 g.), ethyl 2-(2-nitro-3-chlorophenyl)acetate (12.2 g.), anhydrous potassium carbonate (7.5 g.) and dry dimethylformamide (50 ml.) was stirred for an hour at 85° C. The reaction mixture was poured into water (300 ml.) and extracted with diethyl ether. The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate and evaporated under reduced pressure. The oily residue was pulverized and recrystallized from methanol (20 ml.) to give the captioned compound (11.6 g.). mp 78° to 80° C.

Workup

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customrecrystallized from methanol (20 ml.)
  6. customto give the captioned compound (11.6 g.)

Sources & evidence

ORD record
ord-f6205a97ba82492d90ee4456caafdaa1
Source dataset
uspto-grants-1984_09
Patent number
US04472433

Reaction notes

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