3-Aminopropionitrile → N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxamide

HRID 264841Notes

Reaction equation

HRID 264841 reaction equation
[F:1][CH2:2][C:3]1([CH2:19][F:20])[CH:8]=[C:7]([C:9]([OH:11])=O)[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4]1.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:33]([CH2:35][CH2:36][NH2:37])#[N:34].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:33]([CH2:35][CH2:36][NH:37][C:9]([C:7]1[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4][C:3]([CH2:19][F:20])([CH2:2][F:1])[CH:8]=1)=[O:11])#[N:34]

Participants

6

Reactant 4

HCID 16473-AminopropionitrileHCID 11430Potassium CarbonateHCID 682631,1'-CarbonyldiimidazoleHCID 211949872,2-bisfluoromethyl-6-nitro-2H-1-benzopyran-4-carboxylic acid

Product 1

HCID 10735656N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 30 mg of 2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxylic acid and 2 ml of tetrahydrofuran was added 28 mg of 1,1'-carbonyldiimidazole with stirring under ice-cooling and the mixture was stirred for 1 hour. Then, 0.10 ml of 2-cyanoethylamine was added therein, and the resultant mixture was stirred under ice-cooling for 1 hour and subsequently at room temperature for 12 hours. An aqueous potassium carbonate solution was added therein and the reaction solution was extracted with methylene chloride. An organic layer was washed with water and dried, and the solvent was distilled. The resultant residue was recrystallized by a mixed solvent of ethyl acetate and hexane to obtain 26.6 mg of N-(2-cyanoethyl)-2,2-bis(fluoromethyl)-6-nitro-2H-1-benzopyran-4-carboxamide with a melting point of 173°-174° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 1 hour
  3. extractionthe reaction solution was extracted with methylene chloride
  4. washAn organic layer was washed with water
  5. customdried
  6. distillationthe solvent was distilled
  7. customThe resultant residue was recrystallized by a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-2c886468288a49fab2a841ec8481cd64
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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