Sodium Sulfite → HCID 10393036, compound

HRID 2108109Notes

Reaction equation

HRID 2108109 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:36][CH3:37])=[CH:5][C:6]2S[CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:35]=1.ClC1C=CC=C(C(OO)=O)C=1.[S:49]([O-:52])([O-])=[O:50].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]([O:36][CH3:37])=[CH:5][C:6]2[S:49](=[O:52])(=[O:50])[CH2:11][CH2:10][C:9]([C:13]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:34])[C:22]4[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=4)[CH2:17][CH2:16]3)=[O:14])=[CH:8][C:7]=2[CH:35]=1

Participants

6

Reactant 4

HCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 10098451HCID 10098451, compound

Product 1

HCID 10393036HCID 10393036, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In methylene chloride (10 ml) is dissolved 1-(7,8-dimethoxy-2,3-dihydro-1-benzothiepin-4-carbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine (1.6 g) obtained in Working Example 24. To the solution is added, while stirring under ice-cooling, m-chloro-perbenzoic acid (1.71 g) in limited amounts. The mixture is stirred for one hour, and then left standing at -5° C. for 15 hours. To the reaction mixture is added an aqueous solution of acid sodium sulfite to decompose the excess peracid. The resultant is poured into an aqueous solution of sodium hydrogencarbonate; this is followed by extraction with methylene chloride. The organic layer is washed with an aqueous solution of sodium hydrogencarbonate, dried, and concentrated under reduced pressure. The residue is recrystallized from ethanol to give 1-(7,8-dimethoxy-1,1-dioxo-2,3-dihydro-1-benzothiepin4-carbonyl)-4-(3,4,5-trimethoxybenzoyl)piperazine as colorless prisms (1.4 g), m.p. 226°-229° C.

Workup

  1. customobtained in Working Example 24
  2. additionTo the solution is added
  3. temperaturecooling
  4. stirringThe mixture is stirred for one hour
  5. waitleft
  6. extractionthis is followed by extraction with methylene chloride
  7. washThe organic layer is washed with an aqueous solution of sodium hydrogencarbonate
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customThe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-d434a0253b3844b98a1d60582e08d8d0
Source dataset
uspto-grants-1990_06
Patent number
US04937246

Reaction notes

Loading…