Acetyl chloride → HCID 53660605, compound

HRID 1757561Notes

Reaction equation

HRID 1757561 reaction equation
[OH:1][C:2]1[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[C:16]([OH:23])=[C:15]([CH3:24])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([S:13][CH3:14])=[S:12])[CH2:7][CH2:6]1.C(N([CH2:30][CH3:31])CC)C.[C:32](Cl)(=[O:34])[CH3:33].C(=O)([O-])[OH:37].[Na+]>ClCCl>[C:32]([O:1][C:2]1[C:18]([O:19][CH3:20])=[C:17]([O:21][CH3:22])[C:16]([O:23][C:30](=[O:37])[CH3:31])=[C:15]([CH3:24])[C:3]=1[CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11]([S:13][CH3:14])=[S:12])[CH2:7][CH2:6]1)(=[O:34])[CH3:33]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 19388426HCID 19388426, compound

Product 1

HCID 53660605HCID 53660605, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

In a nitrogen atmosphere, 0.50 g (1.34 mmol.) of methyl 4-(2,5-dihydroxy-3,4-dimethoxy-6-methylbenzyl)-1-piperazinecarbodithioate was dissolved in 5 ml of dichloromethane. To the resulting solution was added 0.30 g (2.96 mmol.) of triethylamine. The solution was then chilled with ice, and to the chilled solution was dropwise added a solution of 0.25 g (2.96 mmol.) of 95%-acetyl chloride in 3 ml of dichloromethane. Themixture was then stirred for 6 hours. To the mixture were then added 10 ml of dichloromethane and a small amount of a saturated aqueous sodium hydrogen carbonate solution. The mixture was well shaken, and the organic solvent potitoh was taken out. The organic portion was dried over anhydrous sodium sulfate and placed under reduced pressure to give 0.63 g of methyl 4-(2,5-diacetoxy-3,4-dimethoxy-6-methylbenzyl)-1-piperazinecarbodithioate as an oil.

Workup

  1. temperatureThe solution was then chilled with ice
  2. stirringThe mixture was well shaken
  3. dry with materialThe organic portion was dried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-d2746d6cb45e42959970591d04b5f12b
Source dataset
uspto-grants-1995_08
Patent number
US05446146

Reaction notes

Loading…