Hydrogen Sulfide → HCID 12906352, compound

HRID 1390676Notes

Reaction equation

HRID 1390676 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-fd1ef8b289eb4a7cb885ee2ce0fd2027
Source dataset
uspto-grants-1979_02
Patent number
US04139711

Reaction notes

Loading…