4-Fluoro-3-nitrotoluene → Ethyl 2-(4-methyl-2-nitroanilino)benzo[b]thiophene-3-carboxylate

HRID 649898Notes

Reaction equation

HRID 649898 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].F[C:17]1[CH:22]=[CH:21][C:20]([CH3:23])=[CH:19][C:18]=1[N+:24]([O-:26])=[O:25]>CS(C)=O>[CH3:23][C:20]1[CH:21]=[CH:22][C:17]([NH:1][C:2]2[S:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[C:3]=2[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:18]([N+:24]([O-:26])=[O:25])[CH:19]=1

Participants

4

Reactant 2

HCID 1362874-Fluoro-3-nitrotolueneHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylate

Product 1

HCID 18422341Ethyl 2-(4-methyl-2-nitroanilino)benzo[b]thiophene-3-carboxylateYield 100.9%

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-carboxlate (4.0 g), 4-fluoro-3-nitrotoluene (3.3 g) and dimethyl sulfoxide (55 ml), ethyl 2-(4-methyl-2-nitroanilino)benzo[b]thiophene-3-carboxylate (6.5 g) was obtained.

Workup

  1. customMaterial Synthesis Example 4

Sources & evidence

ORD record
ord-033e2e78be75422387245c0cc595c7ad
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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