Water → Tert-butyl 2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}hydrazinecarboxylate

HRID 1892533Notes

Reaction equation

HRID 1892533 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1C=CN=C1)=[O:2].[C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])(=[O:16])[NH:14]N.NCC[C:25]1[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=1.O>O1CCCC1>[OH:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:11][CH2:12][NH:8][C:1]([NH:3][NH:14][C:13]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[O:2])=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 5610TyramineHCID 682631,1'-CarbonyldiimidazoleHCID 70091tert-Butyl carbazate

Product 1

HCID 58112047Tert-butyl 2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}hydrazinecarboxylateYield 81.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 1,1′-carbonyldiimidazole (1.621 g, 9.994 mmol) in anhydrous tetrahydrofuran (20 ml) was added tert-butyl carbazate (1.322 g, 10.00 mmol), and the mixture was stirred at room temperature for 1.5 hr. 4-(2-Aminoethyl)phenol (1.371 g, 9.991 mmol) was added and the mixture was stirred at room temperature for 6 hr. Water (40 ml) was added to the reaction mixture and the precipitate was collected by filtration, washed 3 times with water and twice with ethyl acetate, and dried under reduced pressure to give tert-butyl 2-{[2-(4-hydroxyphenyl)ethyl]carbamoyl}hydrazinecarboxylate (2.417 g, 8.184 mmol, yield 81.9%) as a white solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 6 hr
  2. filtrationthe precipitate was collected by filtration
  3. washwashed 3 times with water
  4. dry with materialtwice with ethyl acetate, and dried under reduced pressure

Sources & evidence

ORD record
ord-1a6c22ce119d4b3c8fc900456d2b8b78
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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