Methanethiol → HCID 19010372, compound

HRID 1741613Notes

Reaction equation

HRID 1741613 reaction equation
CO.[H-].[Na+].[CH3:5][SH:6].Cl[CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([C:19]2[NH:20][C:21](=[O:28])[C:22]([CH:25]([CH3:27])[CH3:26])([CH3:24])[N:23]=2)[N:10]=1>C(O)(=O)C>[CH:25]([C:22]1([CH3:24])[C:21](=[O:28])[NH:20][C:19]([C:11]2[N:10]=[C:9]([CH2:8][S:6][CH3:5])[CH:18]=[CH:17][C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[N:23]1)([CH3:27])[CH3:26]

Participants

6

Reactant 4

HCID 878MethanethiolHCID 887MethanolHCID 24758Sodium hydrideHCID 19010314HCID 19010314, compound

Product 1

HCID 19010372HCID 19010372, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To 30 mL of absolute methanol, stirred at -10° under nitrogen, is added in portions 0.9 g of 50% sodium hydride (oil dispersion). A stream of methyl mercaptan is then added to the solution until a pH of 10 is achieved. To this solution is added 3 g of methyl 6-chloromethyl-2-(4-isopropyl-4-methyl-5-oxo-2-imidazolin-2-yl)nicotinate, and stirring is continued at -10° for 1 hour. The reaction is then allowed to warm to room temperature over 1 hour, and is then acidified with glacial acetic acid to pH 4. The mixture is concentrated in vacuo, and the residue is dissolved in methylene chloride, washed with saturated aqueous sodium bicarbonate, dried, and concentrated in vacuo. The residue is dissolved in absolute methanol, washed with hexanes, and concentrated in vacuo to afford the desired product. Recrystallization from methylene chloride-hexane affords a solid, mp 113.5°-115° C.

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. dissolutionthe residue is dissolved in methylene chloride
  3. washwashed with saturated aqueous sodium bicarbonate
  4. customdried
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue is dissolved in absolute methanol
  7. washwashed with hexanes
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-82b2eed4e0bb4b45a680749892748230
Source dataset
uspto-grants-1994_08
Patent number
US05334576

Reaction notes

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