1,1'-Thiocarbonyldiimidazole → HCID 9952107, compound

HRID 1590161Notes

Reaction equation

HRID 1590161 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C@H:4]([CH2:20][SH:21])[NH:5][CH2:6][C:7]([S:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)([CH3:9])[CH3:8].[C:23](N1C=CN=C1)(N1C=CN=C1)=[S:24]>C(Cl)(Cl)Cl>[CH3:19][O:18][C:15]1[CH:14]=[CH:13][C:12]([CH2:11][S:10][C:7]([CH3:9])([CH3:8])[CH2:6][N:5]2[C@H:4]([C:3]([O:2][CH3:1])=[O:22])[CH2:20][S:21][C:23]2=[S:24])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 10472632HCID 10472632, compound

Product 1

HCID 9952107HCID 9952107, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of N-[2-(4-methoxybenzylthio)-2-methylpropyl]-L-cysteine methyl ester (5.0 g) in chloroform (90 ml), thiocarbonyldiimidazole (3.0 g) was added and the mixture was stirred for 1 hr at room temperature. The reaction mixture was washed with 3N hydrochloric acid, water and then saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated in vacuo. The crude product was recrystallized from ethyl acetate to give 5.1 g (91%) of the titled compound.

Workup

  1. washThe reaction mixture was washed with 3N hydrochloric acid, water
  2. dry with materialsaturated sodium chloride solution, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe crude product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-582cbd7c56f44b3997d7facf5a900022
Source dataset
uspto-grants-1993_04
Patent number
US05202342

Reaction notes

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