Water → HCID 86616917, compound

HRID 1781965Notes

Reaction equation

HRID 1781965 reaction equation
[OH:1][N:2]=[C:3]1[CH:7]=[CH:6][S:5][C:4]1=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:9]#[N:10].[CH2:18]([S:21](Cl)(=[O:23])=[O:22])[CH2:19][CH3:20].C(N(CC)CC)C.O>O1CCCC1.ClCCl>[CH2:18]([S:21]([O:1][N:2]=[C:3]1[CH:7]=[CH:6][S:5][C:4]1=[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])[C:9]#[N:10])(=[O:23])=[O:22])[CH2:19][CH3:20]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 662791-Propanesulfonyl chlorideHCID 86616752HCID 86616752, compound

Product 1

HCID 86616917HCID 86616917, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 490 g of tetrahydrofuran were dissolved 45 g (0.19 mol) of (3-(hydroxy)imino-3H-thiophen-2-ylidene)-(2-methylphenyl)-acetonitrile in Synthesis Example 1 and 27.0 g (0.19 mol) of commercially available propanesulfonyl chloride. To the solution cooled, 20.6 g (0.20 mol) of triethylamine was added dropwise such that the temperature might not exceed 10° C. The solution was allowed to ripen for 1 hour at room temperature, after which 150 g of water and 500 g of dichloromethane were added. The organic layer was separated, and washed with 150 g of water three times. The organic layer was concentrated in vacuum. Methanol was added to the concentrate for recrystallization, followed by filtration and drying. There were obtained crude yellow crystals. The crude yellow crystals were purified by silica gel column chromatography (eluent, dichloromethane). The elute was concentrated, followed by recrystallization from methanol, filtration and drying. There was obtained 77 g of yellow crystals (yield 70%).

Workup

  1. temperatureTo the solution cooled
  2. customexceed 10° C
  3. customThe organic layer was separated
  4. washwashed with 150 g of water three times
  5. concentrationThe organic layer was concentrated in vacuum
  6. additionMethanol was added to the
  7. concentrationconcentrate for recrystallization
  8. filtrationfollowed by filtration
  9. customdrying
  10. customThere were obtained crude yellow crystals
  11. customThe crude yellow crystals were purified by silica gel column chromatography (eluent, dichloromethane)
  12. concentrationThe elute was concentrated
  13. customfollowed by recrystallization from methanol, filtration
  14. customdrying

Sources & evidence

ORD record
ord-817cd11527084050ab0e75f85e5e8e0a
Source dataset
uspto-grants-2009_03
Patent number
US07498126B2

Reaction notes

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