Benzene → HCID 20238404, compound

HRID 745885Notes

Reaction equation

HRID 745885 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-:3])=[O:2].C([SH:24])C.[CH:25]1[CH:30]=CC=CC=1.C(Cl)(=O)C1C=CC=CC=1>C(OCC)C>[N+:1]([C:4]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:9][C:5]=1[C:6]([O:7][CH2:30][CH3:25])=[S:24])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 6343EthanethiolHCID 7412Benzoyl chlorideHCID 130202985-(2,4-Dichlorophenoxy)-2-nitrobenzoyl chloride

Product 1

HCID 20238404HCID 20238404, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 2-nitro-5-(2',4'-dichlorophenoxy)benzoyl chloride (4.16 g., 0.012 mole) and ethanethiol (2.24 g., 0.036 mole) in 40 ml. benzene was heated at reflux for 2 hours and 50 minutes and then cooled. The mixture was diluted with diethyl ether, washed twice with 10% aqueous NaOH, once with NaCl solution, dried, and evaporated to dryness to give 4.2 g. of an oil. Infrared analysis showed a large amount of initial benzoyl chloride and some desired product. The oil was dissolved in 100 ml. benzene and 3.0 g. ethanethiol and about 1.5 g. triethylamine were added. A precipitate formed immediately. The reaction mixture was refluxed for 1.5 hours, cooled, filtered and evaporated to dryness to give 4.65 g. of the desired product.

Workup

  1. temperatureat reflux for 2 hours and 50 minutes
  2. temperaturecooled
  3. washwashed twice with 10% aqueous NaOH, once with NaCl solution
  4. customdried
  5. customevaporated to dryness
  6. customto give 4.2 g

Sources & evidence

ORD record
ord-c2c8f516b9d8476ba7469ffd5fa2d78b
Source dataset
uspto-grants-1986_07
Patent number
USRE032215

Reaction notes

Loading…