Hydrochloric Acid → Ethyl 2-(2-amino4,5-dichloroanilino)benzo[b]thiophene-3-carboxylate

HRID 649925

Reaction equation

HRID 649925 reaction equation
NC1SC2C=CC=CC=2C=1C(OCC)=O.ClC1C=C(Cl)C(Cl)=CC=1[N+]([O-])=O.[Cl:28][C:29]1[C:49]([Cl:50])=[CH:48][C:32]([NH:33][C:34]2[S:38][C:37]3[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=3[C:35]=2[C:43]([O:45][CH2:46][CH3:47])=[O:44])=[C:31]([N+:51]([O-])=O)[CH:30]=1.Cl.[Sn+2]>C(O)C.CS(C)=O>[NH2:51][C:31]1[CH:30]=[C:29]([Cl:28])[C:49]([Cl:50])=[CH:48][C:32]=1[NH:33][C:34]1[S:38][C:37]2[CH:39]=[CH:40][CH:41]=[CH:42][C:36]=2[C:35]=1[C:43]([O:45][CH2:46][CH3:47])=[O:44]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 69832,4,5-TrichloronitrobenzeneHCID 104883Stannous cationHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylateHCID 18422321Ethyl 2-(4,5-dichloro-2-nitroanilino)benzo[b]thiophene-3-carboxylate

Product 1

HCID 18422259Ethyl 2-(2-amino4,5-dichloroanilino)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), 2,4,5-trichloronitrobenzene (6.8 g) and dimethyl sulfoxide (70 ml), crude crystals (10.3 g) of ethyl 2-(4,5-dichloro-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 (100 ml), 18% hydrochloric acid (100 ml) and tin(II) chlorihe.dihydrate (22.8 g), ethyl 2-(2-amino4,5-dichloroanilino)benzo[b]thiophene-3-carboxylate (5.3 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-bae2b5fabbff4958b6a11fea86e5a88f
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Linked notes

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