Hydrazine hydrate (1:1) → HCID 21702037, compound

HRID 1596402Notes

Reaction equation

HRID 1596402 reaction equation
O.[NH2:2][NH2:3].[C:4]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Cl)=[O:10])([CH3:7])([CH3:6])[CH3:5]>C(O)C>[C:4]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH:2][NH2:3])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21702025tert-butyl N-(3-(chloromethyl)phenyl)carbamate

Product 1

HCID 21702037HCID 21702037, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

While a solution of hydrazine monohydrate (1.32 g, 26.4 m mol) in ethanol (20 ml) was heated under reflux, a solution of 3-tert-butoxycarbonylaminobenzyl chloride (1.06 g, 4.4 m mol) in ethanol (10 ml) was added dropwise thereto over a period of 5 minutes. After this mixture was further refluxed for 0.5 hour, the solvent was distilled off under reduced pressure. The resulting oily residue was extracted with ether (2×20 ml). After the extract was concentrated under reduced pressure, the resulting residue was subjected to chromatography on silica gel (50 g) using chloroform-methanol (10:1), so that the desired compound (0.91 g, 87%) was obtained as an oily material.

Workup

  1. temperatureunder reflux
  2. temperatureAfter this mixture was further refluxed for 0.5 hour
  3. distillationthe solvent was distilled off under reduced pressure
  4. extractionThe resulting oily residue was extracted with ether (2×20 ml)
  5. concentrationAfter the extract was concentrated under reduced pressure

Sources & evidence

ORD record
ord-abbd89455b0c4f519222e7fc503423fa
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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