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

HRID 57147Notes

Reaction equation

HRID 57147 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 (4N, 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-626b6cd4cc0e4d49ac6b51aec4d2648e
Source dataset
uspto-grants-2016_09
Patent number
US09434711B2

Reaction notes

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