Phenylhydrazine → HCID 67171244, compound

HRID 545228Notes

Reaction equation

HRID 545228 reaction equation
C(N(CC)CC)C.Cl[C:9]1[C:14]([C:15]([O:17]CC)=O)=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=1.[C:22]1([NH:28][NH2:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>O1CCCC1>[CH3:21][S:20][C:11]1[N:10]=[C:9]2[N:28]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[NH:29][C:15](=[O:17])[C:14]2=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 7516PhenylhydrazineHCID 8471TriethylamineHCID 800084-Chloro-2-(methylthio)pyrimidine-5-carboxylic acid ethyl ester

Product 1

HCID 67171244HCID 67171244, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

60 mL of triethylamine was added to tetrahydrofuran (200 mL) solution of 25 g of ethyl 4-chloro-2-(methylthio)pyrimidine-5-carboxylate and 12.7 mL of phenylhydrazine, and stirred at room temperature for 18 hours. The solvent was concentrated under reduced pressure, water was added to the residue, then washed with ether, and made acidic with aqueous 5 N hydrochloric acid solution added thereto. The precipitated solid was taken out through filtration, and washed with water and 2-propanol to obtain 10.8 g of the entitled compound as a white solid.

Workup

  1. concentrationThe solvent was concentrated under reduced pressure, water
  2. additionwas added to the residue
  3. washwashed with ether
  4. additionadded
  5. filtrationThe precipitated solid was taken out through filtration
  6. washwashed with water and 2-propanol

Sources & evidence

ORD record
ord-ab77269b6af74996bb52dd11f2365420
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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