1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 23044549, compound

HRID 2165280Notes

Reaction equation

HRID 2165280 reaction equation
O.[Cl:2][CH2:3][CH:4]=[O:5].[N+:6]([CH2:8][C:9]([NH2:11])=[O:10])#[C-:7].N12CCCN=C1CCCCC2>CO>[Cl:2][CH2:3][CH:4]1[O:5][CH:7]=[N:6][CH:8]1[C:9]([NH2:11])=[O:10]

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12227820Acetaldehyde, chloro-, hydrateHCID 206649162-Isocyanoacetamide

Product 1

HCID 23044549HCID 23044549, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

114 g of chloroacetaldehyde monohydrate, and 84 g of isocyanoacetamide were dissolved in 1000 ml of methanol. The mixture was cooled to 0°-3° C. and a solution of 38 g of 1,8-diazabicyclo[5.4.0]undec-7-ene in 200 ml of methanol was added with string. At this temperature. stirring was continued for 30 minutes, and, after removal of the cooling bath, for an additional hour. The solvent was removed in vacuo and the residue refluxed twice with 1000 ml each time of ethyl acetate. The combined hot extracts were treated with charcoal, filtered while still hot and evaporated to yield the title compound as a crystalline residue, melting point 110°-112° C. after recrystallization from ethyl acetate.

Workup

  1. temperatureThe mixture was cooled to 0°-3° C.
  2. customafter removal of the cooling bath
  3. waitfor an additional hour
  4. customThe solvent was removed in vacuo
  5. temperaturethe residue refluxed twice with 1000 ml each time of ethyl acetate
  6. additionThe combined hot extracts were treated with charcoal
  7. filtrationfiltered while still hot and
  8. customevaporated

Sources & evidence

ORD record
ord-4e793792b70d4cb1a6a430f6d00d0bca
Source dataset
uspto-grants-1990_07
Patent number
US04939253

Reaction notes

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