2,4-Dichloronitrobenzene → Ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylate

HRID 649895Notes

Reaction equation

HRID 649895 reaction equation
[NH2:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12].Cl[C:17]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>CS(C)=O>[Cl:23][C:21]1[CH:20]=[CH:19][C:18]([N+:24]([O-:26])=[O:25])=[C:17]([CH:22]=1)[NH:1][C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 118992,4-DichloronitrobenzeneHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylate

Product 1

HCID 18422161Ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylateYield 47%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 4 and using ethyl 2-aminobenzo[b]thiophene-3-carboxylate (4.0 g), 2,4-dichloronitrobenzene (3.8 g) and dimethyl sulfoxide (55 ml), ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (3.2 g) was obtained.

Workup

  1. customMaterial Synthesis Example 4

Sources & evidence

ORD record
ord-c96d41ceea2d4b84b7efed03245abfc6
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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