Ethylene Glycol → HCID 22461012, compound

HRID 1937412Notes

Reaction equation

HRID 1937412 reaction equation
[Na].[CH2:2]([OH:5])[CH2:3][OH:4].Cl[C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:33])([CH3:32])[CH2:24][O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C:8]=1[C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][CH:35]=1.[Cl-].[NH4+]>C(OCC)(=O)C>[OH:4][CH2:3][CH2:2][O:5][C:7]1[N:12]=[CH:11][N:10]=[C:9]([NH:13][S:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]([CH3:33])([CH3:32])[CH2:24][O:25][CH:26]3[CH2:31][CH2:30][CH2:29][CH2:28][O:27]3)=[CH:19][CH:18]=2)(=[O:16])=[O:15])[C:8]=1[C:34]1[CH:35]=[CH:36][C:37]([CH3:40])=[CH:38][CH:39]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 11827385HCID 11827385, compound

Product 1

HCID 22461012HCID 22461012, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

Sodium (35.65 g) is gradually added to ethylene glycol (1.3 liter) at 23-75° C., and thereto is added N-[6-chloro-5-(4-methylphenyl)pyrimidin-4-yl]-4-[2-(2-tetrahydropyranyloxy)-1,1-dimethylethyl]benzenesulfonamide (160 g) at 4° C. The mixture is stirred at 100° C. for 16 hours, and allowed to cool to room temperature. The reaction mixture is poured into a mixture of a saturated aqueous ammonium chloride solution and ethyl acetate under ice-cooling, and the mixture is extracted with ethyl acetate. The extract is washed with a saturated aqueous sodium chloride solution, and the organic layer is dried over anhydrous sodium sulfate and activated carbon. The solid materials are removed by filtration through a Celite pad, and the filtrate is concentrated under reduced pressure. The residue is crystallized from ethyl acetate-diisopropyl ether to give N-[6-(2-hydroxyethoxy)-5-(4-methylphenyl)-pyrimidin-4-yl]-4-[2-(2-tetrahydropyranyloxy)-1,1-dimethyl-ethyl]benzenesulfonamide (80.26 g) as colorless crystals. In addition, the mother liquor is concentrated, and the resultant is recrystallized from ethyl acetate-diisopropyl ether to give the crystals of the above compound (73.1 g).

Workup

  1. temperatureto cool to room temperature
  2. temperaturecooling
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe extract is washed with a saturated aqueous sodium chloride solution
  5. dry with materialthe organic layer is dried over anhydrous sodium sulfate and activated carbon
  6. customThe solid materials are removed by filtration through a Celite pad
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customThe residue is crystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record
ord-3dd2c817485e4ed0abd7d3f8bfec2c54
Source dataset
uspto-grants-2002_05
Patent number
US06395741B1

Reaction notes

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