Dichloromethane → HCID 11799781, compound

HRID 1885611Notes

Reaction equation

HRID 1885611 reaction equation
ClC1C=C(S[CH2:10][CH:11]([C:18](=[O:30])[N:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])C=CC=1Cl.[Cl:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34](C(OO)=O)[CH:33]=1.[S:42]([O-:45])([O-])=[O:43].[Na+].[Na+].[Cl:48]CCl>>[Cl:48][C:37]1[CH:36]=[C:35]([S:42]([CH2:10][CH:11]([C:18](=[O:30])[N:19]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:12][CH2:13][C:14]([O:16][CH3:17])=[O:15])(=[O:45])=[O:43])[CH:34]=[CH:33][C:32]=1[Cl:31]

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 24437Sodium SulfiteHCID 70297m-Chloroperbenzoic acidHCID 11798789HCID 11798789, compound

Product 1

HCID 11799781HCID 11799781, compound

Conditions

Temperature
0 °C

Procedure

Into a solution of methyl 5-(3,4-dichlorophenylthio)-4-(N,N-dipentylcarbamoyl)pentanoate (54.3 g) in dry dichloromethane (500 ml) were added portions of m-chloroperbenzoic acid (80%, 59.5 g) with stirring at 0° C. After stirring at room temperature for 4 hours, sodium sulfite was added. The reaction mixture was washed with a saturated sodium bicarbonate solution and water, dried over MgSO4, and concentrated in vacuo. The residue was recrystallized from hexane to give 49.5 g of methyl 5-(3,4-dichlorophenylsulfonyl)-4-(N,N-dipentylcarbamoyl)pentanoate.

Workup

  1. stirringAfter stirring at room temperature for 4 hours
  2. washThe reaction mixture was washed with a saturated sodium bicarbonate solution and water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-28f2dedc853f44fe8fc812f5bcd7c8e9
Source dataset
uspto-grants-1992_09
Patent number
US05145869

Reaction notes

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