Ethyl Acetate → HCID 58119388, compound

HRID 2167489Notes

Reaction equation

HRID 2167489 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:29]=[CH:28][C:23]([C:24](OC)=[O:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1.CCOC(C)=O.[NH2:36][NH2:37]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:11][C:10]=2[C:20]2[CH:29]=[CH:28][C:23]([C:24]([NH:36][NH2:37])=[O:25])=[CH:22][CH:21]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 9321HydrazineHCID 58119307HCID 58119307, compound

Product 1

HCID 58119388HCID 58119388, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3-oxazol-4-yl}benzoate from Step B (33 mg, 0.077 mmol) was suspended in 1 mL of EtOH and 0.5 mL of anhydrous hydrazine, and heated to reflux for 2 h. EtOAc was added and washed with water 3 times. The organics were dried (MgSO4), and concentrated to afford 4-{5-[(4-chlorophenyl)thio]-2-phenyl-1,3-oxazol-4-yl}benzohydrazide which was used with out further purification. LCMS: m/z 421.1 (M+H)+.

Workup

  1. temperatureto reflux for 2 h
  2. washwashed with water 3 times
  3. dry with materialThe organics were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-90b47972f92e44ff9da867c2f561c502
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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