Hydrogen Sulfide → HCID 12906352, compound

HRID 461224Notes

Reaction equation

HRID 461224 reaction equation
[C:1]([CH:3]1[CH:12]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[CH:5]([C:6]3[C:11]2=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH2:4]1)#[N:2].[CH2:19](N)[CH2:20][NH2:21].S.O>CCOCC>[NH:2]1[CH2:19][CH2:20][N:21]=[C:1]1[CH:3]1[CH:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[CH:5]([C:18]3[C:13]2=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:4]1

Participants

6

Reactant 4

HCID 402Hydrogen SulfideHCID 962WaterHCID 3301EthylenediamineHCID 2403063008-09-1

Product 1

HCID 12906352HCID 12906352, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 11-cyano-9,10-dihydro-9,10-ethanoanthracene (4.6 g), ethylenediamine (1.5 g) and hydrogen sulfide (about 100 mg) is stirred at 130° C for 20 hours. The reaction mixture is mixed with water and ether to be distributed in two layers. The ether layer is washed with water, dried, and evaporated to remove the ether. The residue is recrystallized from ether to give 11-(2-imidazolin-2-yl)-9,10-dihydro-9,10-ethanoanthracene (5.0 g) as crude crystals. IR (KBr), 1621 cm-1 (N--C=N).

Workup

  1. washThe ether layer is washed with water
  2. customdried
  3. customevaporated
  4. customto remove the ether
  5. customThe residue is recrystallized from ether

Sources & evidence

ORD record
ord-39e5bc081f03454eba413a4a36d426d7
Source dataset
uspto-grants-1977_12
Patent number
US04061854

Reaction notes

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