Triethylamine → HCID 12906308, compound

HRID 2059000Notes

Reaction equation

HRID 2059000 reaction equation
[C:1]1([CH2:9]Br)[C:2]([CH2:7]Br)=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH3:11][N:12]([NH2:20])[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].C(N(CC)CC)C>CN(C)C=O.O>[C:16]([O:15][C:13]([N:12]([CH3:11])[N:20]1[CH2:7][C:2]2[C:1](=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 66665o-Bis(bromomethyl)benzeneHCID 37482801-Boc-1-methylhydrazine

Product 1

HCID 12906308HCID 12906308, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A vigorously stirred solution 13.15 g (0.05 mole) of o-xylylene dibromide and 7.3 g (0.05 mole) of t-butyl 2-methylcarbazate in 25 ml of dimethylformamide was warmed to 50° and 14 ml of triethylamine was added during 5-8 minutes while maintaining the temperature at 50°-60°. After complete addition the reaction mixture was stirred at room temperature for 3 hrs. and diluted with 100 ml of water. After stirring for 1 hr the mixture was extracted with ethyl acetate. The organic phase was separated and dried. Filtration and evaporation gave a gummy solid which was used without further purification. The IR and NMR of the material were consistent with the proposed structure.

Workup

  1. temperaturewhile maintaining the temperature at 50°-60°
  2. additionAfter complete addition the reaction mixture
  3. stirringAfter stirring for 1 hr the mixture
  4. extractionwas extracted with ethyl acetate
  5. customThe organic phase was separated
  6. customdried
  7. filtrationFiltration and evaporation
  8. customgave a gummy solid which
  9. customwas used without further purification

Sources & evidence

ORD record
ord-70a6271643af4583b258b62aac8c190f
Source dataset
uspto-grants-1982_03
Patent number
US04321200

Reaction notes

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