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Water → 1-[4-(3-Mercapto-2-mercaptomethyl-2-methyl-propylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one

HRID 376972
Notes
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Reaction equation

HRID 376972 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:17])([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1.[SH:19][CH2:20][C:21]([CH2:25][SH:26])([CH2:23][SH:24])[CH3:22].[H-].[Na+].O>CN(C)C=O>[SH:19][CH2:20][C:21]([CH2:25][SH:26])([CH3:22])[CH2:23][S:24][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[C:9]([CH3:17])([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[CH3:10])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 115138141,3-Propanedithiol, 2-(mercaptomethyl)-2-methyl-HCID 154053051-(4-Fluorphenyl)-2-methyl-2-morpholino-1-propanone

Product 1

HCID 193606041-[4-(3-Mercapto-2-mercaptomethyl-2-methyl-propylthio)-phenyl]-2-methyl-2-morpholin-4-yl-propan-1-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3.6 g (14.3 mmol) of 1-(4-fluorophenyl)-2-methyl-2-morpholin-4-yl-propan-1-one and 12 g (71.3 mmol) of 1,1,1-trismercaptomethylethane are dissolved in 70 ml of dry dimethylformamide, and 28.6 mmol of sodium hydride are added. The solution is stirred at room temperature for 2 h. Then the solution is poured into water. The crude product is extracted with methylene chloride, washed with water, dried over MgSO4, and concentrated. The residue is purified by column chromatography on silica gel with methylene chloride as an eluent. The structure is confirmed by the 1H-NMR spectrum (CDCl3): δ [ppm] 1.12 (s, 3H), 1.30 (t, 2H), 1.31 (s, 6H), 2.57 (t, 4H), 2.62-2.72 (m, 4H), 3.14 (s, 2H), 3.69 (t, 4H), 7.33 (d, 2H), 8.49 (d, 2H).

Workup

  1. extractionThe crude product is extracted with methylene chloride
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue is purified by column chromatography on silica gel with methylene chloride as an eluent

Sources & evidence

ORD record
ord-1aebfafd823e4b548631e7f95a3d8730
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06022906

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes