Water → HCID 21997580, compound

HRID 1977261Notes

Reaction equation

HRID 1977261 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][NH2:17])=[O:15])=[CH:12][CH:11]=1.N1C=CC=CC=1.[CH3:26][O:27][C:28]([C:30]1[CH:38]=[CH:37][C:33]([C:34](Cl)=[O:35])=[CH:32][CH:31]=1)=[O:29].O>O1CCCC1>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([NH:16][NH:17][C:34](=[O:35])[C:33]2[CH:32]=[CH:31][C:30]([C:28]([O:27][CH3:26])=[O:29])=[CH:38][CH:37]=2)=[O:15])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 21997501HCID 21997501, compound

Product 1

HCID 21997580HCID 21997580, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-(6-methoxy-n-hexyloxy)benzohydrazide (106.82 g) and pyridine (162 ml) in tetrahydrofuran (1 L) at 0°‥5° C. was treated portionwise with 4-methoxycarbonylbenzoyl chloride 83.75 g) over 30 minutes. After a further 1 hour at 0°-5° C., and 2 hours at room temperature, tlc indicated completed reaction and the reaction mixture was poured into water (7 L). The resulting precipitate was collected by filtration, washed thoroughly with water, and dried under hi-vacuum at 50° C. to give N-[4-(6-methoxy-n-hexyloxy)benzoyl]-N′-(4-methoxycarbonylbenzoyl)hydrazine (171.0 g) as a white solid.

Workup

  1. custom2 hours
  2. customat room temperature
  3. customreaction
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed thoroughly with water
  6. customdried under hi-vacuum at 50° C.

Sources & evidence

ORD record
ord-a42fcf94beca42839dc09aef7a3ec94b
Source dataset
uspto-grants-2001_05
Patent number
US06232290B1

Reaction notes

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