Hydrochloric Acid → Ethyl 2-(6-amino-2,3-dichloroanilino)benzo[b]thiophene-3-carboxylate

HRID 649927

Reaction equation

HRID 649927 reaction equation
NC1SC2C=CC=CC=2C=1C(OCC)=O.ClC1C(Cl)=C(Cl)C=CC=1[N+]([O-])=O.[Cl:28][C:29]1[C:49]([Cl:50])=[CH:48][CH:47]=[C:46]([N+:51]([O-])=O)[C:30]=1[NH:31][C:32]1[S:36][C:35]2[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=2[C:33]=1[C:41]([O:43][CH2:44][CH3:45])=[O:42].Cl.[Sn+2]>C(O)C.CS(C)=O>[NH2:51][C:46]1[C:30]([NH:31][C:32]2[S:36][C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[C:33]=2[C:41]([O:43][CH2:44][CH3:45])=[O:42])=[C:29]([Cl:28])[C:49]([Cl:50])=[CH:48][CH:47]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 286972,3,4-TrichloronitrobenzeneHCID 104883Stannous cationHCID 699464Ethyl 2-amino-1-benzothiophene-3-carboxylateHCID 18422195HCID 18422195, compound

Product 1

HCID 18422327Ethyl 2-(6-amino-2,3-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 (6.6 g), 2,3,4-trichloronitrobenzene (7.0 g) and dimethyl sulfoxide (70 ml), crude crystals (12 g) of ethyl 2-(2,3-dichloro-6-nitroanilino)benzo[b]thiophene-3-carboxylate were obtained. Without purification, in the same manner as in Starting Material Synthesis Example 21 and using ethanol (40 ml), 18% hydrochloric acid (60 ml) and tin(II) chlorihe.dihydrate (24.6 g), ethyl 2-(6-amino-2,3-dichloroanilino)benzo[b]thiophene-3-carboxylate (4.2 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-0fa18393955e4de78421b40daf32cca1
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Linked notes

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