Hydrochloric Acid → HCID 57042257, compound

HRID 851571Notes

Reaction equation

HRID 851571 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:17]([N+]([O-])=O)=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=[CH:14][C:13]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([N+]([O-])=O)[C:26]=1[C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][C:38]=1[Cl:47].[SH-:48].[Na+].Cl.[SH2:51]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12]1[C:17]([SH:48])=[C:16]([N+:21]([O-:23])=[O:22])[CH:15]=[CH:14][C:13]=1[O:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[C:27]([SH:51])[C:26]=1[C:37]1[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][C:38]=1[Cl:47]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 402Hydrogen SulfideHCID 28015Sodium hydrosulfideHCID 20251543HCID 20251543, compound

Product 1

HCID 57042257HCID 57042257, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

18 g of Compound 1 was dissolved in 100 ml of tetrahydrofuran. To this solution was dropped 200 ml of a sodium hydrosulfide solution* over 1 hour in a stream of nitrogen gas. After the dropping, the solution was agitated for further 4 hours at room temperature, to which was added dilute hydrochloric acid while ice-cooling until it became slightly acidic. Nitrogen gas was violently injected into the solution to expel the liberated hydrogen sulfide, followed by extraction with benzene. The benzene extract was washed with water, dried and treated under reduced pressure to distill off the solvent. Then it was purified by a chromatography using a silica gel column (solvent: benzene/hexane=1/1) to obtain 15 g of Compound 12 (yield 87%).

Workup

  1. temperaturecooling until it
  2. extractionfollowed by extraction with benzene
  3. extractionThe benzene extract
  4. washwas washed with water
  5. customdried
  6. additiontreated under reduced pressure
  7. distillationto distill off the solvent
  8. customThen it was purified by a chromatography

Sources & evidence

ORD record
ord-e07ad09f74284348a111d20be2f7b77a
Source dataset
uspto-grants-1983_05
Patent number
US04385189

Reaction notes

Loading…