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

HRID 2405859Notes

Reaction equation

HRID 2405859 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-2e01fff0fd5445198a2aa660059ee9a1
Source dataset
uspto-grants-2014_08
Patent number
US08809327B2

Reaction notes

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