Benzene → 2',4,4',5-Tetrachloropyrrole-2-carboxanilide

HRID 2083126Notes

Reaction equation

HRID 2083126 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]([OH:10])=O)[NH:5][C:6]=1[Cl:7].S(Cl)(Cl)=O.C1C=CC=CC=1.[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[NH2:24]>N1C=CC=CC=1>[Cl:21][C:22]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:23]=1[NH:24][C:8]([C:4]1[NH:5][C:6]([Cl:7])=[C:2]([Cl:1])[CH:3]=1)=[O:10]

Participants

6

Reactant 4

HCID 241BenzeneHCID 111232,4-DichloroanilineHCID 24386Thionyl ChlorideHCID 162274944,5-Dichloro-1H-pyrrole-2-carboxylic acid

Product 1

HCID 203598762',4,4',5-Tetrachloropyrrole-2-carboxanilide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4,5-Dichloropyrrole-2-carboxylic acid (10 g., 0.056 mole) was converted to the corresponding acid chloride by reaction with 15 ml. of thionyl chloride, and the acid chloride dissolved in 25 ml. of benzene was reacted with 9.2 g. (0.057 mole) of 2,4-dichloroaniline in 50 ml. of pyridine using the procedure described above in Example 3. The product was recrystallized from an ethyl acetate/ethanol mixture to give 10.0 of 2',4,4',5-tetrachloropyrrole-2-carboxanilide, m.p. 262°-264° C.

Workup

  1. customThe product was recrystallized from an ethyl acetate/ethanol mixture

Sources & evidence

ORD record
ord-d5c8cc3018eb4c09b3155c49d26e0e80
Source dataset
uspto-grants-1978_04
Patent number
US04084051

Reaction notes

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