Hydrazine, dihydrochloride → HCID 178521699, compound

HRID 1040442Notes

Reaction equation

HRID 1040442 reaction equation
[CH2:1]([O:8][C:9](=[O:21])[NH:10][C:11]1([C:14](=O)/[N:15]=[CH:16]/[N:17](C)C)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.Cl.[NH2:24]N.CCOC(C)=O.O>CC(O)=O>[CH2:1]([O:8][C:9](=[O:21])[NH:10][C:11]1([C:14]2[NH:15][CH:16]=[N:17][N:24]=2)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 17548Hydrazine, dihydrochlorideHCID 22728543Water ethylacetateHCID 178484344HCID 178484344, compound

Product 1

HCID 178521699HCID 178521699, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of (1-{[1-dimethylamino-meth-(E)-ylidene]-carbamoyl}-cyclopropyl)-carbamic acid benzyl ester (1.11 g, 3.83 mmol) in AcOH (6 ml) was added hydrazine dihydrochloride (803 mg, 7.65 mmol). The reaction mixture was stirred at 90° C. for 1.5 h. The reaction mixture was poured into EtOAc/water. The organic phase was separated, washed with water, sat. NaHCO3, brine, dried over anhydrous Na2SO4, filtered, concentrated and dried under high vacuum to afford 677 mg of [1-(4H-[1,2,4]triazol-3-yl)-cyclopropyl]-carbamic acid benzyl ester as a off-white solid, m/z 259.6 [M+1]+.

Workup

  1. customThe organic phase was separated
  2. washwashed with water, sat. NaHCO3, brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-1b7eafbeadd64fb99c81afe6bf06a9ac
Source dataset
uspto-grants-2013_10
Patent number
US08552205B2

Reaction notes

Loading…