Sodium hydride → HCID 20266398, compound

HRID 1719705Notes

Reaction equation

HRID 1719705 reaction equation
[H-].[Na+].[S:3]1(=[O:9])(=[O:8])[CH2:7][CH2:6][CH2:5][NH:4]1.[CH3:10][C:11]1([CH:14]2[CH2:19][CH2:18][N:17]([C:20]3[C:29]4[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=4)[N:23]=[CH:22][N:21]=3)[CH2:16][CH2:15]2)[CH2:13][O:12]1>CN(C=O)C>[OH:12][C:11]([CH:14]1[CH2:19][CH2:18][N:17]([C:20]2[C:29]3[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=3)[N:23]=[CH:22][N:21]=2)[CH2:16][CH2:15]1)([CH3:10])[CH2:13][N:4]1[CH2:5][CH2:6][CH2:7][S:3]1(=[O:9])=[O:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6421571,3-PropanesultamHCID 20266386HCID 20266386, compound

Product 1

HCID 20266398HCID 20266398, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.25 g of a 50% dispersion in oil) was added at room temperature to a stirred solution of isothiazolidine-1,1-dioxide (2.42 g) in DMF (15 cm3). After stirring for 0.5 hours 2-methyl-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]oxirane (5.0 g) was added and the mixture was stirred for 4 hours at 100°. Volatile material was removed in vacuo, the residue was partitioned between chloroform (100 cm3) and water (50 cm3) and the chloroform layer was dried (MgSO4) and evaporated. The residue was chromatographed on silica ("Merck" 60.9385) eluting with methanol:ethyl acetate, 1:4, to give a solid which was recrystallised from ethyl acetate-methanol to give 2-{2-hydroxy-2-[1-(6,7-dimethoxyquinazolin-4-yl)piperid-4-yl]prop-1-yl}isothiazolidine-1,1-dioxide, m.p. 173°-174° (4.15 g).

Workup

  1. additionwas added
  2. customVolatile material was removed in vacuo
  3. customthe residue was partitioned between chloroform (100 cm3) and water (50 cm3)
  4. dry with materialthe chloroform layer was dried (MgSO4)
  5. customevaporated
  6. customThe residue was chromatographed on silica ("Merck" 60.9385)
  7. washeluting with methanol
  8. customethyl acetate, 1:4, to give a solid which
  9. customwas recrystallised from ethyl acetate-methanol

Sources & evidence

ORD record
ord-0ac898f11f384d3ab3f3ae727bbdc046
Source dataset
uspto-grants-1985_09
Patent number
US04542132

Reaction notes

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