Triethylamine → HCID 178510460, compound

HRID 1985696Notes

Reaction equation

HRID 1985696 reaction equation
[N+:1]([C:4]1[CH:15]=[C:8]2[C:9]([O:11][C:12](=O)[NH:13][C:7]2=[CH:6][CH:5]=1)=O)([O-:3])=[O:2].C(#N)C([CH2:19][C:20]#[N:21])O.C([N:25](CC)CC)C>CN(C=O)C>[NH2:25][C:12]1[C:19]([C:20]#[N:21])=[C:9]([OH:11])[C:8]2[C:7](=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:15]=2)[N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 208212H-3,1-Benzoxazine-2,4(1H)-dione, 6-nitro-HCID 212535622-Hydroxybutanedinitrile

Product 1

HCID 178510460HCID 178510460, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 47.25 g of 5-nitroisatoic anhydride in 230 mL of DMF 15 g of malonitrile and 63.3 mL of triethylamine were added and the reaction mixture was stirred at 60° C. for 2 hours. The solvent was evaporated at reduced pressure and the residue was mixed with 570 mL of acetonitrile and 114 mL of concd. HCl and the solution was stirred at room temperature overnight. The precipitate was then filtered off, washed with water and ethanol to give 49.7 g of product, m.p.: >360° C. LC-MS: MH+ 231; Ret. time: 4.78 min.

Workup

  1. customThe solvent was evaporated at reduced pressure
  2. additionthe residue was mixed with 570 mL of acetonitrile and 114 mL of concd
  3. stirringHCl and the solution was stirred at room temperature overnight
  4. filtrationThe precipitate was then filtered off
  5. washwashed with water and ethanol

Sources & evidence

ORD record
ord-c49135927c4d40e8a95c7c92767e8cd1
Source dataset
uspto-grants-2009_06
Patent number
US07547696B2

Reaction notes

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