Acetic Anhydride → HCID 15290080, compound

HRID 1460164Notes

Reaction equation

HRID 1460164 reaction equation
[OH:1][C:2]1[C:18]([OH:19])=[C:17]([OH:20])[CH:16]=[CH:15][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(O[C:25](=[O:27])[CH3:26])(=O)C>C(Cl)(Cl)Cl>[C:2]([O:1][C:2]1[C:18]([O:19][C:18](=[O:19])[CH3:17])=[C:17]([O:20][C:25](=[O:27])[CH3:26])[CH:16]=[CH:15][C:3]=1[CH2:4][N:5]1[CH2:6][CH2:7][N:8]([C:11]([S:13][CH3:14])=[S:12])[CH2:9][CH2:10]1)(=[O:1])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 15290078HCID 15290078, compound

Product 1

HCID 15290080HCID 15290080, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 520 ml of chloroform was suspended 50 g of methyl 4-(2,3,4-trihydroxybenzyl)-1-piperazinecarbodithioate, and to the suspension was dropwise added under chilling with ice 97.3 g of acetic anhydride over a period of 15 min. The mixture was then stirred for one hour. The reaction mixture was washed successively with water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residual oil was crystallized by addition of 250 ml of ethyl acetate. After stirring for one hour, the crystals were collected by filtration. The crystals were washed with ethyl acetate to give 48.8 g of the desired compound as white crystals, m.p. 148°-150° C. (decomp.), yield 69.7%.

Workup

  1. additionto the suspension was dropwise added
  2. washThe reaction mixture was washed successively with water
  3. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  4. customThe sodium sulfate was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residual oil was crystallized by addition of 250 ml of ethyl acetate
  7. stirringAfter stirring for one hour
  8. filtrationthe crystals were collected by filtration
  9. washThe crystals were washed with ethyl acetate

Sources & evidence

ORD record
ord-b66ba8e0bd414c2d97438b212ad04d25
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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