tert-Butyl carbazate → HCID 67842119, compound

HRID 1493221Notes

Reaction equation

HRID 1493221 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-butoxycarbonyl- hydrazino)-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-6a98ae30740e4bd7a2c80c6583918d5b
Source dataset
uspto-grants-1991_06
Patent number
US05021432

Reaction notes

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