Triethylamine → 2',2"'-(Dithio)-bis[5'-chloro-4-ethoxy-3-thiophenecarboxanilide]

HRID 614222Notes

Reaction equation

HRID 614222 reaction equation
[CH2:1]([O:3][C:4]1[C:5]([C:9](Cl)=[O:10])=[CH:6][S:7][CH:8]=1)[CH3:2].[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([S:20][S:21][C:22]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:23]=2[NH2:24])=[C:17]([CH:19]=1)[NH2:18].C(N([CH2:35][CH3:36])CC)C>C(Cl)Cl>[Cl:29][C:26]1[CH:27]=[CH:28][C:22]([S:21][S:20][C:16]2[CH:15]=[CH:14][C:13]([Cl:12])=[CH:19][C:17]=2[NH:18][C:9]([C:5]2[C:4]([O:3][CH2:35][CH3:36])=[CH:8][S:7][CH:6]=2)=[O:10])=[C:23]([CH:25]=1)[NH:24][C:9]([C:5]1[C:4]([O:3][CH2:1][CH3:2])=[CH:8][S:7][CH:6]=1)=[O:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 947422,2'-Dithiobis(5-chloroaniline)HCID 125737274-Ethoxy-3-thiophenecarbonyl chloride

Product 1

HCID 867363882',2"'-(Dithio)-bis[5'-chloro-4-ethoxy-3-thiophenecarboxanilide]

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 6.60 g. portion of 4-ethoxy-3-thiophenecarbonyl chloride in 50 ml of methylene chloride is added dropwise to a solution of 5.48 g. of 2,2'-(dithio)bis[5-chloroaniline] and 3.54 g. of triethylamine in 100 ml of methylene chloride as in Example 14. After filtration through magnesium silicate, the filtrate was concentrated to dryness and the residue was recrystallized from methylene chloride:petroleum ether to give 2',2"'-(dithio)-bis[5'-chloro-4-ethoxy-3-thiophenecarboxanilide] as yellow crystals, m.p. 179°-181° C.

Workup

  1. filtrationAfter filtration through magnesium silicate
  2. concentrationthe filtrate was concentrated to dryness
  3. customthe residue was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-dff199ebefec4b989be18ae78904f4df
Source dataset
uspto-grants-1979_03
Patent number
US04144235

Reaction notes

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