Hydrochloric Acid → Benzo[b]thiophen-2-amine hydrochloride

HRID 1691544Notes

Reaction equation

HRID 1691544 reaction equation
C(OC(=O)[NH:7][C:8]1[S:12][C:11]2[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=2[CH:9]=1)(C)(C)C.[ClH:18]>O1CCOCC1>[ClH:18].[S:12]1[C:8]([NH2:7])=[CH:9][C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13182766tert-butyl N-(1-benzothiophen-2-yl)carbamate

Product 1

HCID 66906726Benzo[b]thiophen-2-amine hydrochlorideYield 83%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Compound 1-B (1.45 g, 5.81 mmol) was added to a solution of HCl in dioxane (4 N, 20 mL), and the mixture was stirred at rt until all the starting material was consumed. The mixture was diluted with diethyl ether, the product collected by filtration, and washed with diethyl ether, to afford compound 1-C as an off-white solid (0.89 g, 83%). 1H-NMR (DMSO-d6): δ 6.43 (s, 1H), 6.8-7.2 (br s, 3H) superimposed on 7.05 (m, 1H) and 7.20 (m, 1H), 7.45 (d, 1H), 7.66 (d, 1H); MS: m/z 150.1 (MH+).

Workup

  1. customwas consumed
  2. additionThe mixture was diluted with diethyl ether
  3. filtrationthe product collected by filtration
  4. washwashed with diethyl ether

Sources & evidence

ORD record
ord-95777b88e7c545408d7c862013dabda4
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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