Triethylamine → HCID 19000467, compound

HRID 2260428Notes

Reaction equation

HRID 2260428 reaction equation
Cl[CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][C:3]1=[O:8].[CH3:9][C:10]([C:13]1[CH:14]=[C:15]([SH:23])[CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)([CH3:12])[CH3:11].C(N(CC)CC)C>O1CCCC1>[CH3:12][C:10]([C:13]1[CH:14]=[C:15]([S:23][CH:2]2[CH2:7][CH2:6][CH2:5][CH2:4][C:3]2=[O:8])[CH:16]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:18]=1)([CH3:9])[CH3:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 132032-ChlorocyclohexanoneHCID 14795713HCID 14795713, compound

Product 1

HCID 19000467HCID 19000467, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Chlorocyclohexanone (0.6 g, 0.0045 moles) was added to a cold (+5° C.) solution of 3,5-bis (1,1-dimethylethyl)benzenethiol (Example 2)(1.0 g, 0.0045 moles) in tetrahydrofuran (50 ml). The solution was stirred for 15 minutes. Triethylamine (1.25 ml) was added, the cold bath was removed and the mixture was stirred at room temperature for 20 hours and then at 50° C. for 2 hours. The mixture was cooled to room temperature and filtered to remove a white solid. The filtrate was concentrated to an oil. The product was purified by silica gel chromatography to give a white solid which was recrystallized from hexane (DSC 81.49° C.). The structure was supported by NMR and Ir.

Workup

  1. customthe cold bath was removed
  2. stirringthe mixture was stirred at room temperature for 20 hours
  3. waitat 50° C. for 2 hours
  4. filtrationfiltered
  5. customto remove a white solid
  6. concentrationThe filtrate was concentrated to an oil
  7. customThe product was purified by silica gel chromatography
  8. customto give a white solid which
  9. customwas recrystallized from hexane (DSC 81.49° C.)

Sources & evidence

ORD record
ord-50ac17aa27244f96a7e61a78de6c4737
Source dataset
uspto-grants-1995_12
Patent number
US05476944

Reaction notes

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