Diphenyl Ether → HCID 22282664, compound

HRID 1374949Notes

Reaction equation

HRID 1374949 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[S:12][CH2:11][CH2:10][C:8]3=2)[CH:3]=[CH:2]1.CCCCCCC.C1(OC2C=CC=CC=2)C=CC=CC=1>CCCCCCC.ClCCl>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]3[S:12][CH2:11][CH2:10][C:8]3=2)[CH:3]=[CH:2]1.[S:1]1[C:5]2[CH:6]=[C:7]3[C:8]([CH2:10][CH2:11][NH:12]3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 3

HCID 7583Diphenyl EtherHCID 8900Heptane2×HCID 22282676HCID 22282676, compound

Product 2

HCID 22282664HCID 22282664, compoundYield 41%HCID 22282676HCID 22282676, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

7,8-Dihydrothieno[2,3-g]indole, 5,6-dihydrothieno[3,2-f] and 5,6-dihydrothieno[2,3-e]indole were prepared according to the method described in Example 3, using the above mixture of dihydrothienoindole-2-carboxylic acids (1.64 g, 7.48 mmol), with the following modification. After the mixture had been passed down the heptane-packed column and the phenyl ether flushed-off with heptane, the eluant was increased to heptane-dichloromethane (1:1→1:3) to afford a purple solid. The solid was recrystallised [heptane-isopropyl ether (1:1)] to afford a mixture (2:3) of 7,8-dihydrothieno[2,3-g]indole and 5,6-dihydrothieno[3,2-f]indole (540 mg, 41%) as a pink solid. The filtrate was evaporated to afford a mixture (25:30:45) of 7,8-dihydrothieno[2,3-g]indole, 5,6-dihydrothieno[3,2-f]indole and 5,6-dihydrothieno[2,3-e]indole (644 mg, 49%) as a purple solid which was used without further purification.

Workup

  1. customto afford a purple solid
  2. customThe solid was recrystallised [heptane-isopropyl ether (1:1)]

Sources & evidence

ORD record
ord-10efd335e0274ba685073503f56b7cde
Source dataset
uspto-grants-2007_01
Patent number
US07166632B2

Reaction notes

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