tert-Butyl carbazate → HCID 67842119, compound

HRID 1108966Notes

Reaction equation

HRID 1108966 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH:9]3[O:14][CH:8]3[C:7]=2[CH:15]=1)#[N:2].[C:16]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])(=[O:19])[NH:17][NH2:18]>C(O)C>[C:21]([O:20][C:16]([NH:17][NH:18][C@@H:8]1[C:7]2[CH:15]=[C:3]([C:1]#[N:2])[CH:4]=[CH:5][C:6]=2[O:11][C:10]([CH3:13])([CH3:12])[C@H:9]1[OH:14])=[O:19])([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 108673602,2-Dimethyl-3,4-epoxy-6-cyanochroman

Product 1

HCID 67842119HCID 67842119, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6-Cyano-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (8.0 g) and tert-butyl carbazate (6.3 g) were dissolved in 40 ml of ethanol and the solution was heated under reflux for 28 hours. The resulting ethanol was distilled off and the residue was recrystallized from 80 ml of hexane and 8 ml of ethanol to yield 8.7 g of trans-4-(2-tert-butoxycarbonylhydrazino)-6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-3-ol as white crystals, m.p. 136°-138° C.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 28 hours
  3. distillationThe resulting ethanol was distilled off
  4. customthe residue was recrystallized from 80 ml of hexane and 8 ml of ethanol

Sources & evidence

ORD record
ord-8630d265560c4cc9bb7515b87fb06e2f
Source dataset
uspto-grants-1994_06
Patent number
US05318969

Reaction notes

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