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Ethyl Acetate → 4-[3-(2-Chloro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

HRID 2075688
Notes
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Reaction equation

HRID 2075688 reaction equation
O=[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[NH:3]1.CCOC(C)=O.C([O-])(O)=O.[Na+].P(Cl)(Cl)([Cl:40])=O>>[Cl:40][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12][C:13]3[CH:14]=[C:15]([C:19]4([C:25]#[N:26])[CH2:24][CH2:23][O:22][CH2:21][CH2:20]4)[CH:16]=[CH:17][CH:18]=3)[CH:8]=2)[N:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 589265284-[3-(2-Oxo-1,2-dihydro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Product 1

HCID 582577564-[3-(2-Chloro-quinolin-6-ylsulfanyl)-phenyl]-tetrahydro-pyran-4-carbonitrile

Conditions

Temperature
90 °C

Procedure

5g (4.52 g, 12.5 mmol) was dissolved in phosphorus oxychloride (23 mL) and heated to 90° C. for 1 hour. The reaction was cooled to room temperature, and ice was added slowly, followed by EtOAc and NaHCO3. The aqueous layer was extracted with CH2Cl2 twice, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the desired product, 5h.

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. additionice was added slowly
  3. extractionThe aqueous layer was extracted with CH2Cl2 twice
  4. dry with materialthe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7655124af6f24b7691511f0d5bf17073
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07919621B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes