HCID 23053854, compound → HCID 13649684, compound

HRID 280659Notes

Reaction equation

HRID 280659 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([Cl:12])[C:10]=1Cl)[C:5]([NH2:7])=[O:6].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S-:20])=[CH:16][CH:15]=1.[K+]>CN(C)C=O>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:10]2[C:9]([Cl:12])=[CH:8][C:4]([C:5]([NH2:7])=[O:6])=[CH:3][C:2]=2[Cl:1])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 23053854HCID 23053854, compoundHCID 23693160HCID 23693160, compound

Product 1

HCID 13649684HCID 13649684, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,4,5-trichlorobenzamide (25.0 g, 111 mmol) and potassium 4-chlorothiophenolate (29.0 g, 159 mmol) in dimethylformamide (220 ml) was stirred for 3 days at ambient temperature under nitrogen atmosphere, poured into ice water (2.2 L), and filtered. The solid was washed with water, partially dried under vacuum, suspended in diethyl ether (200 ml), filtered, and washed with diethyl ether (2×75 ml). The residue was triturated with diethyl ether (75 ml), filtered, again triturated with diethyl ether (75 ml), filtered, and dried under vacuum to provide 21.2 g (57%) of 4-(4-chlorophenylthio)-3,5-dichlorobenzamide, m.p. 171°-174° C.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with water
  3. custompartially dried under vacuum
  4. filtrationfiltered
  5. washwashed with diethyl ether (2×75 ml)
  6. customThe residue was triturated with diethyl ether (75 ml)
  7. filtrationfiltered
  8. customagain triturated with diethyl ether (75 ml)
  9. filtrationfiltered
  10. customdried under vacuum

Sources & evidence

ORD record
ord-5b10938079df4a19a660590971585767
Source dataset
uspto-grants-1986_05
Patent number
US04590201

Reaction notes

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