Triethylamine → [2,3-bis(Acetyloxy)benzoyl]hydrazinecarboxylic acid, t-butyl ester

HRID 2292377Notes

Reaction equation

HRID 2292377 reaction equation
[C:1]([O:5][C:6]([NH:8][NH2:9])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:17]([O:20][C:21]1[C:29]([O:30][C:31](=[O:33])[CH3:32])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23](Cl)=[O:24])(=[O:19])[CH3:18]>ClCCl>[C:17]([O:20][C:21]1[C:29]([O:30][C:31](=[O:33])[CH3:32])=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[NH2:9])=[O:24])(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 70091tert-Butyl carbazateHCID 156204123-(Chlorocarbonyl)-1,2-phenylene diacetate

Product 1

HCID 86742713[2,3-bis(Acetyloxy)benzoyl]hydrazinecarboxylic acid, t-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-[(t-Butyloxy)carbonyl]hydrazine (12 g) and 10 g of triethylamine were dissolved in 200 ml of dichloromethane and, at 0° C., 24 g of 2,3-bis(acetyloxy)benzoyl chloride in 50 ml of dichloromethane was added dropwise with stirring (30 minutes). After continuous stirring for one hour, the reaction mixture was extracted with 200 ml of ice water, 50 ml of 1% sodium bicarbonate and 100 ml of 5% citric acid. The organic phase was then washed with 100 ml of water, dried over sodium sulfate, and the solvent distilled off. The remaining oil crystallized after stirring with hexane. The result was beige crystals, 26.3 g; melting point 117° C.

Workup

  1. stirringAfter continuous stirring for one hour
  2. extractionthe reaction mixture was extracted with 200 ml of ice water, 50 ml of 1% sodium bicarbonate and 100 ml of 5% citric acid
  3. washThe organic phase was then washed with 100 ml of water
  4. dry with materialdried over sodium sulfate
  5. distillationthe solvent distilled off
  6. customThe remaining oil crystallized
  7. stirringafter stirring with hexane

Sources & evidence

ORD record
ord-4adfd776424044dba590eaa0c1e1cf75
Source dataset
uspto-grants-1989_01
Patent number
US04801705

Reaction notes

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