Butanethiol → HCID 20497973, compound

HRID 2166833Notes

Reaction equation

HRID 2166833 reaction equation
[CH2:1]([SH:5])[CH2:2][CH2:3][CH3:4].C[O-].[Na+].Cl.Cl[CH:11]([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20].[NH4+].[OH-]>CO.C(OCC)(=O)C.O>[CH2:1]([S:5][CH:11]([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 8012ButanethiolHCID 14923Ammonium HydroxideHCID 10942334Sodium MethoxideHCID 70531060HCID 70531060, compound

Product 1

HCID 20497973HCID 20497973, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent3×HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Butyl mercaptan, 4.32 g (0.048 mole), was added to a solution of 2.376 g (0.044 mole) sodium methoxide in 100 ml of methanol and the mixture stirred 30 minutes followed by addition of 10.0 g (0.032 mole) of 1-(α-chloro-2,4-dichlorophenethyl) imidazole hydrochloride in 100 ml methanol. The total mixture was heated to reflux for 4 hours. After cooling, the mixture was poured into an excess of H2O and the organic layer extracted with ether. The combined ether extracts were washed with 10% NaOH, with H2O, then dried over MgSO4, and filtered. Dry HCl gas was passed through the ether solution to give an oily liquid. Trituration of the oily salt in ethyl acetate was not successful in giving a solid product. The oily salt was dissolved in methanol, treated with excess NH4OH, and converted back to the free base. A total of 4.35 g (42.3%) of the free base was recovered. H1 nmr: DMSO δ TMS 7.38 (m, 6H, aryl/imidazole; 4.6 (m, 3H, CH/CH2), 0.6 to 2.76 (m, 9H, C4H9).

Workup

  1. temperatureThe total mixture was heated
  2. temperatureto reflux for 4 hours
  3. temperatureAfter cooling
  4. extractionthe organic layer extracted with ether
  5. washThe combined ether extracts were washed with 10% NaOH, with H2O
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customto give an oily liquid
  9. customin giving a solid product
  10. customA total of 4.35 g (42.3%) of the free base was recovered

Sources & evidence

ORD record
ord-d33a5756d1994c4bb8cc4035cd4bdc35
Source dataset
uspto-grants-1983_06
Patent number
US04389409

Reaction notes

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