Water → N-4-hexylbenzoyl-N'-(6-acetoxy-2-naphthoyl)hydrazine

HRID 1534761Notes

Reaction equation

HRID 1534761 reaction equation
C([C:7]1[CH:16]=[CH:15][C:10]([C:11]([NH:13][NH2:14])=[O:12])=[CH:9][CH:8]=1)CCCCC.[C:17]([O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][CH:30]=1)[CH:27]=[C:26]([C:31](Cl)=[O:32])[CH:25]=[CH:24]2)(=[O:19])[CH3:18].N1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.O.O1CCOC[CH2:42]1>>[CH3:35][CH2:36][CH2:37][CH:38]([N:13]([C:11](=[O:12])[C:10]1[CH:9]=[CH:8][CH:7]=[CH:16][CH:15]=1)[NH:14][C:31]([C:26]1[CH:25]=[CH:24][C:23]2[C:28](=[CH:29][CH:30]=[C:21]([O:20][C:17](=[O:19])[CH3:18])[CH:22]=2)[CH:27]=1)=[O:32])[CH2:39][CH3:42]

Participants

6

Reactant 5

HCID 962WaterHCID 1049PyridineHCID 312751,4-DioxaneHCID 126805484-HexylbenzohydrazideHCID 157248096-(Chlorocarbonyl)naphthalen-2-yl acetate

Product 1

HCID 67795738N-4-hexylbenzoyl-N'-(6-acetoxy-2-naphthoyl)hydrazineYield 87%

Conditions

Temperature
83 °C

Procedure

In a 100 ml-three-necked flask, 1.30 g (5.90 mM) of 4-hexylbenzohydrazide was placed and a solution of the above-prepared 6-acetoxy-2-naphthoyl chloride in 45 ml of dioxane was added thereto, followed by heating to about 83° C. To the mixture, 2.20 ml of pyridine was added under stirring, followed by stirring for 25 minutes at 83°-83.5° C. After the reaction, the reaction mixture was cooled on an iced water bath and poured into 300 ml of iced water to precipitate a crystal. The crystal was recovered by filtration, followed by washing with water and further washing with methanol to obtain 2.22 g of N-4-hexylbenzoyl-N'-(6-acetoxy-2-naphthoyl)hydrazine (Yield: 87.0%). ##STR33##

Workup

  1. stirringby stirring for 25 minutes at 83°-83.5° C
  2. customAfter the reaction
  3. temperaturethe reaction mixture was cooled on an iced water bath
  4. customto precipitate a crystal
  5. filtrationThe crystal was recovered by filtration
  6. washby washing with water
  7. washfurther washing with methanol

Sources & evidence

ORD record
ord-7de115d4076842d28f915d8325be9448
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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