Thionyl Chloride → HCID 20321559, compound

HRID 866506Notes

Reaction equation

HRID 866506 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:16])[N:10]=[CH:11][C:12]=2[C:13](O)=O)=[C:4]([CH:17]([O:25][CH3:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH:3]=1.S(Cl)(Cl)=O.C([N:34](C(C)C)CC)(C)C>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH3:16])[N:10]=[CH:11][C:12]=2[CH2:13][NH2:34])=[C:4]([CH:17]([O:25][CH3:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[CH:3]=1

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 20321543HCID 20321543, compound

Product 1

HCID 20321559HCID 20321559, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of 7.8 g of 3-[4-chloro-2-(2-chloro-α-methoxy-benzyl)-phenyl]-2-methylpyrazole-4-carboxylic acid in 75 ml of methylene chloride and 6.7 ml diisopropyl ethylamine is stirred in an ice bath and 4.7 ml of thionyl chloride are added. The mixture is refluxed for 40 minutes, cooled and washed with icewater. The organic layer is dried, evaporated and the residue taken up in 65 ml of tetrahydrofuran and the solution saturated with ammonia. After stirring at 25° for 16 hours, the mixture is diluted in diethyl ether, washed with water and brine, dried and evaporated. The resdiue is dissolved in 300 ml of diethyl ether and the solution refluxed for 16 hours with 2 g of lithium aluminum hydride. After destroying the excess reagent and filtering off the precipitate, the filtrate is washed with diluted hydrochloric acid. The acidic layer is basified with aqueous sodium hydroxide and extracted with methylene chloride. The extract is dried, evaporated, the residue taken up in ethyl acetate and the solution acidified with hydrogen chloride, to yield the 3-[4-chloro-2-(2-chloro-α-methoxy-benzyl)-phenyl]-4-aminomethyl-2-methylpyrazole hydrochloride melting at 260°-262°.

Workup

  1. temperatureThe mixture is refluxed for 40 minutes
  2. temperaturecooled
  3. washwashed with icewater
  4. customThe organic layer is dried
  5. customevaporated
  6. additionthe mixture is diluted in diethyl ether
  7. washwashed with water and brine
  8. customdried
  9. customevaporated
  10. dissolutionThe resdiue is dissolved in 300 ml of diethyl ether
  11. temperaturethe solution refluxed for 16 hours with 2 g of lithium aluminum hydride
  12. customAfter destroying the excess reagent
  13. filtrationfiltering off the precipitate
  14. washthe filtrate is washed with diluted hydrochloric acid
  15. extractionextracted with methylene chloride
  16. customThe extract is dried
  17. customevaporated

Sources & evidence

ORD record
ord-b953b084acb542409a8e2643a13da8e3
Source dataset
uspto-grants-1978_07
Patent number
US04099012

Reaction notes

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