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

HRID 841843Notes

Reaction equation

HRID 841843 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

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 6342AcetonitrileSolvent

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.

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-ae77e55afd61442eb35d21089d65bfb5
Source dataset
uspto-grants-2002_04
Patent number
USRE037664E1

Reaction notes

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