Dimethylformamide → HCID 70028380, compound

HRID 1635479Notes

Reaction equation

HRID 1635479 reaction equation
[C:1]1([C:7]2[C:8]3[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=3[O:10][CH2:11][C:12]=2[CH:13]=[CH:14][C:15](O)=[O:16])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.C(Cl)(=O)C(Cl)=O.[CH3:33][S:34][C:35]1[C:40]([NH2:41])=[C:39]([S:42][CH3:43])[CH:38]=[C:37]([CH3:44])[N:36]=1>C(Cl)Cl.O.N1C=CC=CC=1>[CH3:33][S:34][C:35]1[C:40]([NH:41][C:15](=[O:16])[CH:14]=[CH:13][C:12]2[CH2:11][O:10][C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[C:7]=2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[C:39]([S:42][CH3:43])[CH:38]=[C:37]([CH3:44])[N:36]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 99903926-Methyl-2,4-bis-methylsulfanylpyridin-3-ylamineHCID 70025873HCID 70025873, compound

Product 1

HCID 70028380HCID 70028380, compoundYield 66.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

1 g (3.59 mmol) of 3-(4-phenyl-2H-3-benzo[b]pyranyl)prop-2-enoic acid in solution in 30 ml of methylene chloride is placed in a 250-ml reactor protected from moisture, and a drop of dimethylformamide is added thereto. 0.39 ml (3.76 mmol) of oxalyl chloride is poured dropwise into this solution kept at room temperature. The reaction medium is then heated under reflux for 1 hour. After evaporation of the solvent, the reaction medium is taken up in 20 ml of methylene chloride. This solution is then poured into a mixture kept between 0 and 5° C. consisting of 0.75 g (3.76 mmol) of 2,4-dimethylthio-6-methyl-3-pyridylamine, 2.2 ml of pyridine and 30 ml of methylene chloride. The resulting reaction medium is stirred at room temperature for 12 hours. After addition of water, the organic phase is separated after settling out, washed with a 2 normal hydrochloric acid solution and then with water until a pH of the washings equal to 7 is obtained. After drying over sodium sulfate, the organic phase is evaporated off. The resulting solid is dispersed in 10 ml of hexane and drained. 1.1 g of the expected compound are thus obtained in the crude state. The latter is recrystallized from 140 ml of ethanol (12 hours at −20° C.) and then drained and dried. 0.77 g of the expected compound is obtained, that is to say a yield of 46.7%. This compound has a melting point of between 225 and 227° C.

Workup

  1. additionis added
  2. customkept at room temperature
  3. temperatureThe reaction medium is then heated
  4. temperatureunder reflux for 1 hour
  5. customAfter evaporation of the solvent
  6. additionThis solution is then poured into a mixture
  7. customkept between 0 and 5° C.
  8. customThe resulting reaction medium
  9. customthe organic phase is separated
  10. washwashed with a 2 normal hydrochloric acid solution
  11. customwith water until a pH of the washings equal to 7 is obtained
  12. dry with materialAfter drying over sodium sulfate
  13. customthe organic phase is evaporated off
  14. additionThe resulting solid is dispersed in 10 ml of hexane

Sources & evidence

ORD record
ord-3631031d1ba0453e8e77184845b34fc8
Source dataset
uspto-grants-2003_01
Patent number
US06509362B2

Reaction notes

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