3-(Acetylsulfanyl)propanoyl chloride → HCID 13773256, compound

HRID 1651444Notes

Reaction equation

HRID 1651444 reaction equation
[C:1]1([C:7]2[S:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17]([S:20][CH2:21][CH2:22][C:23](Cl)=[O:24])(=[O:19])[CH3:18]>C1(C)C=CC=CC=1>[C:17]([S:20][CH2:21][CH2:22][C:23]([N:9]1[N:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[S:11][CH:10]1[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:24])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 129431223-(Acetylsulfanyl)propanoyl chlorideHCID 23051224HCID 23051224, compound

Product 1

HCID 13773256HCID 13773256, compoundYield 71.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product of step (a) (2.36g) in toluene (100ml) was treated with polyvinylpyridine (2.0g) and 3-acetylthiopropanoyl chloride (1.7g) and the mixture stirred at room temperature for 4 hours. The mixture was filtered and the filtrate stirred with a saturated solution of sodium bicarbonate (100ml) for 1 hour. The organic phase was separated, washed with water, dried and evaporated to a gum. The residue was purified by flash chromatography to give the sub-title product (2.62g) as an oil.

Workup

  1. filtrationThe mixture was filtered
  2. stirringthe filtrate stirred with a saturated solution of sodium bicarbonate (100ml) for 1 hour
  3. customThe organic phase was separated
  4. washwashed with water
  5. customdried
  6. customevaporated to a gum
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-d71d77da22bf4a6f9b555a107d8f43a7
Source dataset
uspto-grants-1990_05
Patent number
US04927822

Reaction notes

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