Sulfolane → HCID 178527747, compound

HRID 2058247Notes

Reaction equation

HRID 2058247 reaction equation
[N:1]1[C:5]2[C:6]3[C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4]=2[NH:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[S].[S:19]1(CCCC1)(=O)=O>>[NH:1]1[C:5]2[C:6]3[C:11]([C:12]4[CH:13]=[CH:14][CH:15]=[CH:16][C:17]=4[C:4]=2[N:3]=[C:2]1[SH:19])=[CH:10][CH:9]=[CH:8][CH:7]=3

Participants

4

Reactant 3

HCID 31347SulfolaneHCID 674781H-Phenanthro(9,10-d)imidazoleHCID 5362487Sulfur

Product 1

HCID 178527747HCID 178527747, compound

Procedure

Ten grams of the imidazole was suspended in 100 ml of sulfolane (tetramethylene sulfone) and 3 gms of powdered sulfur was added; the resulting mixture was heated in an atmosphere of nitrogen at 200°-205° with thorough stirring for eight hours. The reaction mixture was then cooled, and diluted with 500 ml of ice-cold water. The dark brown mass that separated was collected by filtration and thoroughly washed with water and dried in a vacuum oven at 100° for ten hours. The crude product was purified by column chromatography using basic alumina (Woelm grade 1) and dimethylformamide as the eluent. The purified product was triturated with boiling acetonitrile, melting point above 375°.

Workup

  1. temperaturethe resulting mixture was heated in an atmosphere of nitrogen at 200°-205°
  2. temperatureThe reaction mixture was then cooled
  3. customThe dark brown mass that separated
  4. filtrationwas collected by filtration
  5. washthoroughly washed with water
  6. customdried in a vacuum oven at 100° for ten hours
  7. customThe crude product was purified by column chromatography
  8. customThe purified product was triturated with boiling acetonitrile, melting point above 375°

Sources & evidence

ORD record
ord-66c526df0f9140c29d3eea16da6a36a5
Source dataset
uspto-grants-1980_07
Patent number
US04215135

Reaction notes

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