Hydrochloric Acid → Ethyl 2-(2-amino-4-bromoanilino)benzo[b]thiophene-3-carboxylate

HRID 649922Notes

Reaction equation

HRID 649922 reaction equation
NC1SC2C=CC=CC=2C=1C(OCC)=O.BrC1C=CC(Br)=CC=1[N+]([O-])=O.[Br:27][C:28]1[CH:48]=[CH:47][C:31]([NH:32][C:33]2[S:37][C:36]3[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=3[C:34]=2[C:42]([O:44][CH2:45][CH3:46])=[O:43])=[C:30]([N+:49]([O-])=O)[CH:29]=1.Cl.[Sn](Cl)Cl>C(O)C.CS(C)=O>[NH2:49][C:30]1[CH:29]=[C:28]([Br:27])[CH:48]=[CH:47][C:31]=1[NH:32][C:33]1[S:37][C:36]2[CH:38]=[CH:39][CH:40]=[CH:41][C:35]=2[C:34]=1[C:42]([O:44][CH2:45][CH3:46])=[O:43]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24479Stannous ChlorideHCID 770041,4-Dibromo-2-nitrobenzeneHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylateHCID 18422146Ethyl 2-(4-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylate

Product 1

HCID 18422347Ethyl 2-(2-amino-4-bromoanilino)benzo[b]thiophene-3-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 702EthanolSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 4 and using ethyl 2-aminobenzo[b]thiophene-3-carboxylate (6.0 g), 2,5-dibromonitrobenzene (8.5 g) and dimethyl sulfoxide (70 ml), crude crystals (7.3 g) of ethyl 2-(4-bromo-2-nitroanilino)benzo[b]thiophene-3-carboxylate were obtained. Without purification, in the same manner as in Starting Material Synthesis Example 21 and using ethanol (70 ml), 18% hydrochloric acid (70 ml) and tin(II) chloride.dihydrate (15.7 g), ethyl 2-(2-amino-4-bromoanilino)benzo[b]thiophene-3-carboxylate (3.3 g) was obtained.

Workup

  1. customMaterial Synthesis Example 4
  2. customwere obtained
  3. customWithout purification
  4. customMaterial Synthesis Example 21

Sources & evidence

ORD record
ord-d1472a7893ef471fa5e0ff186ab8c40a
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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