Dichloromethane → HCID 23433766, compound

HRID 2121624Notes

Reaction equation

HRID 2121624 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH3:13])=[N:10][C:9]=2[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:4][N:3]=1.ClCCl.ClC1C=CC=CN=1.[NH2:30][NH2:31]>>[CH3:13][C:11]1[O:12][C:8]([C:5]2[CH:6]=[CH:7][C:2]([NH:30][NH2:31])=[N:3][CH:4]=2)=[C:9]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:10]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 79772-ChloropyridineHCID 9321Hydrazine2×HCID 23433735HCID 23433735, compound

Product 1

HCID 23433766HCID 23433766, compound

Conditions

Temperature
70 °C

Procedure

A mixture of 120 mg of 2-chloro-5-(2-methyl-4-phenyl-oxazol-5-yl)-pyridine in 1 mL of hydrazine (98%) was heated at 70° C. for 45 min before adding 0.5 mL of dichloromethane to get better mixing of the hydrazine and the chloro-pyridine. When the dichloromethane had evaporated 0.5 mL of ethanol was added and the mixture was heated for 11 hours. The layers were separated. The ethanol layer was diluted with ethyl acetate and washed with aqueous sodium carbonate (2×), dried (magnesium sulfate), filtered, and the filtrate was evaporated to give 110 mg of crude 5-(2-Methyl-4-phenyl-oxazol-5-yl)-pyridin-2-yl-hydrazine as an orange solid. This material was used with out purification in the next step.

Workup

  1. customto get better
  2. customWhen the dichloromethane had evaporated 0.5 mL of ethanol
  3. additionwas added
  4. temperaturethe mixture was heated for 11 hours
  5. customThe layers were separated
  6. additionThe ethanol layer was diluted with ethyl acetate
  7. washwashed with aqueous sodium carbonate (2×)
  8. dry with materialdried (magnesium sulfate)
  9. filtrationfiltered
  10. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-1646950dd12b45649f33122c227fbaa9
Source dataset
uspto-grants-2004_02
Patent number
US06696464B2

Reaction notes

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