Lithium hydride → HCID 15700630, compound

HRID 236780

Reaction equation

HRID 236780 reaction equation
[CH:1]([NH:3][C:4]1[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[H-].[Li+].[Al].[Li].[H-].[Al+3].[H-].[H-]>O1CCOCC1.C(Cl)Cl.O>[CH3:1][NH:3][C:4]1[C:5]2[CH:18]=[CH:17][CH:16]=[CH:15][C:6]=2[S:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

9

Reactant 5

HCID 62714Lithium hydrideHCID 3028194LithiumHCID 5359268AluminumHCID 15700625HCID 15700625, compoundHCID 21584524Aluminiumhydride

Product 1

HCID 15700630HCID 15700630, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

3.0 g (11.8 mmol) of 3-formamido-2-phenyl-benzo(b)thiophene and 1.08 g (28.4 mmol) of lithium hydride and aluminium are refluxed with stirring for 30 minutes in 60 milliliters of absolute dioxane. The cooled reaction mixture is mixed with water to decompose the excess lithium and aluminium hydride and, after the addition of approximately 100 milliliters of CH2Cl2, it is stirred for a further 15 minutes. After centrifuging with the addition of the hyflo, the organic phase is dried over K2CO3 and evaporated: 3-methylamino-2-phenyl-benzo(b)thiophene in the form of a crude oily product. It is dissolved in a little CHCl3 and converted into the hydrochloride by hydrochloric gas: 2.6 g (80% of theory) of colourless crystals in a mixture of ethanol and ether, decomposition from 198° C. (in sealed tubes).

Workup

  1. customThe cooled reaction mixture
  2. additionAfter centrifuging with the addition of the hyflo
  3. dry with materialthe organic phase is dried over K2CO3
  4. customevaporated
  5. dissolutionIt is dissolved in a little CHCl3
  6. addition2.6 g (80% of theory) of colourless crystals in a mixture of ethanol and ether, decomposition from 198° C. (in sealed tubes)

Sources & evidence

ORD record
ord-646c84d9ff4b4925bdf2e6ad448a3cd5
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Linked notes

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