Sodium diethyldithiocarbamate trihydrate → 3-(Benzyloxycarbonylamino)-N-[2-[diethylamino(thiocarbonyl)-thio]ethyl]propionamide

HRID 1583509Notes

Reaction equation

HRID 1583509 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18]Br)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.O.[CH2:23]([N:25]([CH2:29][CH3:30])[C:26](=[S:28])[S-:27])[CH3:24].[Na+]>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][S:28][C:26]([N:25]([CH2:29][CH3:30])[CH2:23][CH3:24])=[S:27])=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 517546Sodium diethyldithiocarbamate trihydrateHCID 202587523-(benzyloxycarbonylamino)-N-(2-bromoethyl)propionamide

Product 1

HCID 133361483-(Benzyloxycarbonylamino)-N-[2-[diethylamino(thiocarbonyl)-thio]ethyl]propionamideYield 89.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To the solution of 3-(benzyloxycarbonylamino)-N-(2-bromoethyl)propionamide (10 g) in acetone (250 ml), sodium diethyldithiocarbamate trihydrate (6.8 g) in acetone (150 ml) is added and the mixture is stirred for 40 minutes at room temperature. The reaction mixture is filterd and the filtrate is concentrated in vacuo. The residue is dissolved in ethyl acetate (150 ml) and the solution is washed with N hydrochloric acid, N sodium hydroxide, water and saturated sodium chloride solution in the named order. The ethyl acetate solution is dried over anhydrous magnesium sulfate and concentrated in vacuo to give 10.7 g (89%) of the titled compound.

Workup

  1. concentrationthe filtrate is concentrated in vacuo
  2. dissolutionThe residue is dissolved in ethyl acetate (150 ml)
  3. washthe solution is washed with N hydrochloric acid, N sodium hydroxide, water and saturated sodium chloride solution in the named order
  4. dry with materialThe ethyl acetate solution is dried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d85aec25f98640f0976d1ec51fba414a
Source dataset
uspto-grants-1985_11
Patent number
US04552765

Reaction notes

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