Water → 3-Ethylamino-2-phenyl-benzo(b)thiophene

HRID 236782Notes

Reaction equation

HRID 236782 reaction equation
[C:1]([NH:4][C:5]1[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=O)[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.C(Cl)Cl>O1CCOCC1>[CH2:1]([NH:4][C:5]1[C:6]2[CH:19]=[CH:18][CH:17]=[CH:16][C:7]=2[S:8][C:9]=1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 15700627HCID 15700627, compoundHCID 21226445Aluminium lithium hydride2×

Product 1

HCID 157006313-Ethylamino-2-phenyl-benzo(b)thiophene

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

10.7 g (40 mmol) of 3-acetamido-2-phenyl-benzo(b)thiophene and 3.8 g (0.1 mol) of LiAlH4 in 200 milliliters of absolute dioxan is refluxed with stirring for 1 hour. The cooled reaction mixture is mixed with water to decompose the excess LiAlH4 and, after the addition of 300 milliliters of CH2Cl2, it is stirred for a further 15 minutes. After centrifuging with the addition of hyflo, the organic phase is dried over potassium carbonate and evaporated: 3-ethylamino-2-phenyl-benzo(b)thiophene in the form of a crude oily product. It is dissolved in a little chloroform and converted into the hydrochloride by hydrochloric gas: 10.9 g (94% of theory) of colourless sticks in ethanol, decomposition from 205° C. (in sealed tube).

Workup

  1. customThe cooled reaction mixture
  2. stirringis stirred for a further 15 minutes
  3. additionAfter centrifuging with the addition of hyflo
  4. dry with materialthe organic phase is dried over potassium carbonate
  5. customevaporated
  6. dissolutionIt is dissolved in a little chloroform
  7. customfrom 205° C.

Sources & evidence

ORD record
ord-70da6258de8946ba9e609423515c86d5
Source dataset
uspto-grants-1979_06
Patent number
US04157399

Reaction notes

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