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Potassium Carbonate → N-[4-chloro-3-(3-methoxy-5,6-dihydro-2H-thiopyranyl)-phenyl]-3,4,5,6-tetrahydrophthalimide

HRID 727748
Notes
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Reaction equation

HRID 727748 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1O.ClC[C:22]1[CH2:23][S:24][CH2:25][CH2:26][CH:27]=1.[C:28](=O)([O-])[O-:29].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12](=[O:13])[C:11]3[CH2:14][CH2:15][CH2:16][CH2:17][C:10]=3[C:9]2=[O:18])=[CH:4][C:3]=1[CH:23]1[C:22]([O:29][CH3:28])=[CH:27][CH2:26][CH2:25][S:24]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12769235N-(3-Hydroxy-4-chlorophenyl)-3,4,5,6-tetrahydrophthalimideHCID 156145643-chloromethyl-5,6-dihydro-2H-thiopyran

Product 1

HCID 22617247N-[4-chloro-3-(3-methoxy-5,6-dihydro-2H-thiopyranyl)-phenyl]-3,4,5,6-tetrahydrophthalimide

Reagents, catalysts & solvents 1

HCID 6342Acetonitrile
Solvent

Procedure

13.9 g of N-(4-chloro-3-hydroxyphenyl)-3,4,5,6-tetrahydrophthalimide, 8.2 9 of 3-chloromethyl-5,6-dihydro-2H-thiopyran and 8.3 g of potassium carbonate in 150 ml of acetonitrile are refluxed for hours. The mixture is cooled and filtered, the filtrate is evaporated down, the residue is taken up in 200 ml of methylene chloride and the solution is washed twice with 10% strength sodium hydroxide solution and 3 times with water, dried and evaporated out. 15.0 g of N-[4-chloro-3-(3-methoxy-5,6-dihydro-2H-thiopyranyl)-phenyl]-3,4,5,6-tetrahydrophthalimide (mp. 116-119° C.) are obtained. ##STR20##

Workup

  1. temperatureThe mixture is cooled
  2. filtrationfiltered
  3. customthe filtrate is evaporated down
  4. washthe solution is washed twice with 10% strength sodium hydroxide solution and 3 times with water
  5. customdried
  6. customevaporated out

Sources & evidence

ORD record
ord-88383c4fbf9b479f95587f7cff4b6d1d
Source dataset
uspto-grants-1991_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05045105

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes