Water → N-[4-(5-chloro-2-pyrimidinyloxy)-3-methylphenyl]valeramide

HRID 704318Notes

Reaction equation

HRID 704318 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=2[CH3:16])=[N:6][CH:7]=1.C(N(CC)CC)C.[C:24](Cl)(=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28].O>O1CCCC1>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([O:8][C:9]2[CH:15]=[CH:14][C:12]([NH:13][C:24](=[O:29])[CH2:25][CH2:26][CH2:27][CH3:28])=[CH:11][C:10]=2[CH3:16])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 61186Valeryl chlorideHCID 142078084-((5-Chloropyrimidin-2-yl)oxy)-3-methylaniline

Product 1

HCID 10471221N-[4-(5-chloro-2-pyrimidinyloxy)-3-methylphenyl]valeramide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g of 4-(5-chloro-2-pyrimidinyloxy)-3-methylaniline and 1.3 ml of triethylamine were dissolved in 20 ml of tetrahydrofuran, and 1.12 ml of valeryl chloride was dropwise added thereto under cooling with ice. The mixture was reacted at room temperature for 40 minutes under stirring. After completion of the reaction, the reaction product was poured into water and extracted with ethyl acetate. The extract layer was washed with a saturated aqueous solution of sodium chloride and dried over Glauber's salt. Then, ethyl acetate was distilled off to obtain 2.8 g of N-[4-(5-chloro-2-pyrimidinyloxy)-3-methylphenyl]valeramide (Intermediate Compound No. 13) (melting point: 146°-150° C.)

Workup

  1. temperatureunder cooling with ice
  2. customThe mixture was reacted at room temperature for 40 minutes
  3. customAfter completion of the reaction
  4. extractionextracted with ethyl acetate
  5. washThe extract layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over Glauber's salt
  7. distillationThen, ethyl acetate was distilled off

Sources & evidence

ORD record
ord-0851eff8bf704ab9b703de0c96e7061c
Source dataset
uspto-grants-1991_01
Patent number
US04987135

Reaction notes

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