Potassium Carbonate → Ethyl 2-(2-amino-5-chloroanilino)benzo[b]thiophene-3-carboxylate

HRID 649909Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:23]([O-])=O)=[C:6]([CH:22]=1)[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18].O.O.[Sn](Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>C(O)C.Cl>[NH2:23][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:22][C:6]=1[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[C:9]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

Conditions

Temperature: 30 °C

Procedure

Ethyl 2-(5-chloro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (3.2 g) was suspended in ethanol (40 ml) and a solution obtained by dissolving tin(II) chloride dihydrate (7.7 g) in ethanol (50 ml) and 18% hydrochloric acid (50 ml) was added with stirring the mixture. The mixture was stirred at 60° C. for 2 hr and cooled to 30° C. Potassium carbonate was added until the reaction mixture was basified. After filtering through celite, the filtrate was extracted with ethyl acetate, washed with water and dried over magnesium sulfate. After natural filtration, the solvent was evaporated under reduced pressure to give ethyl 2-(2-amino-5-chloroanilino)benzo[b]thiophene-3-carboxylate (2.6 g).

Workup

customa solution obtained
additionwas added
stirringThe mixture was stirred at 60° C. for 2 hr
filtrationAfter filtering through celite
extractionthe filtrate was extracted with ethyl acetate
washwashed with water
dry with materialdried over magnesium sulfate
filtrationAfter natural filtration
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-7687699e35c14656aeba3f942c81d5e8
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06271225B1

Reaction notes

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