Water → 3,4-dihydro-2H-thieno[3,2-b]indole

HRID 23409

Reaction equation

HRID 23409 reaction equation
[C:1]1([NH:7]N)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[S:9]1[CH2:13][CH2:12][C:11](=O)[CH2:10]1.O>C(O)(=O)C>[S:9]1[C:10]2[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=3[NH:7][C:11]=2[CH2:12][CH2:13]1

Participants

5

Reactant 3

HCID 962WaterHCID 7516PhenylhydrazineHCID 61252Dihydro-3(2H)-thiophenone

Product 1

HCID 225741003,4-dihydro-2H-thieno[3,2-b]indoleYield 48.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of phenylhydrazine (5.0 g, 46 mmole) in acetic acid (50 ml) was added dihydro-thiophen-3-one (4.72 g, 46 mmole) at room temperature. Following an exothermic reaction, the temperature was maintained at 80° C. for 2 h. The reaction mixture was poured into water (300 ml) and the precipitate was filtered. Purification on a short column of aluminum oxide (activity II, 6% water) using t-butylmethylether as the eluting solvent gave pure 3,4-dihydro-2H-thieno[3,2-b]indole as a yellow solid (3.9 g, 48% yield), m.p. 152-155° C. (lit. m.p. 153° C., WO01/12603) Step 2

Workup

  1. customan exothermic reaction
  2. filtrationthe precipitate was filtered
  3. customPurification on a short column of aluminum oxide (activity II, 6% water)

Sources & evidence

ORD record
ord-b57c3233657843b996544f76991d9455
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Linked notes

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