3,4-Dichlorobenzamide → HCID 23320963, compound

HRID 280655Notes

Reaction equation

HRID 280655 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1Cl)[C:5]([NH2:7])=[O:6].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([S-:19])=[CH:15][CH:14]=1.[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[S:19][C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][CH:15]=1)[C:5]([NH2:7])=[O:6]

Participants

4

Reactant 2

HCID 1376713,4-DichlorobenzamideHCID 23693160HCID 23693160, compound

Product 1

HCID 23320963HCID 23320963, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 3,4-dichlorobenzamide (95.0 g, 0.500 mole) in dry dimethylformamide (1 liter) was added in one portion potassium 4-chlorothiophenolate (118.8 g, 0.650 mole). The mixture was stirred under nitrogen at 100° C. for 8 hours and at ambient temperature for 16 hours. Solvent (750 ml) was removed by vacuum distillation at 45° C. and the residue was poured into ice water (3 liters) containing concentrated hydrochloric acid (25 ml). The precipitate was filtered, partially dried, and crystallized from hot ethanol (1.2 liters). The crystals were filtered, washed with ethanol, and dried at 45° C. for 18 hours under vacuum to provide 102.0 g (68%) of 3-chloro-4-(4-chlorophenylthio)benzamide, m.p. 176°-177° C.

Workup

  1. customSolvent (750 ml) was removed by vacuum distillation at 45° C.
  2. additionthe residue was poured into ice water (3 liters)
  3. additioncontaining concentrated hydrochloric acid (25 ml)
  4. filtrationThe precipitate was filtered
  5. custompartially dried
  6. customcrystallized from hot ethanol (1.2 liters)
  7. filtrationThe crystals were filtered
  8. washwashed with ethanol
  9. customdried at 45° C. for 18 hours under vacuum

Sources & evidence

ORD record
ord-bfde7d7c6bd341ffbac57720867f1428
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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