Triethylamine → N,N-Dimethyl-Alpha-Cyano-BetaHydroxy-2-Nitro-4-Trifluoromethylcinnamamide

HRID 2231156Notes

Reaction equation

HRID 2231156 reaction equation
[CH3:1][N:2]([CH3:8])[C:3](=[O:7])[CH2:4][C:5]#[N:6].C(N(CC)CC)C.[N+:16]([C:19]1[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22])([O-:18])=[O:17]>CN(C)C1C=CN=CC=1.C1COCC1>[CH3:1][N:2]([CH3:8])[C:3](=[O:7])[C:4]([C:5]#[N:6])=[C:21]([OH:22])[C:20]1[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[CH:27][C:19]=1[N+:16]([O-:18])=[O:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 2511432-Cyano-N,N-dimethylacetamideHCID 143235242-Nitro-4-(trifluoromethyl)benzoyl chloride

Product 1

HCID 67899390N,N-Dimethyl-Alpha-Cyano-BetaHydroxy-2-Nitro-4-TrifluoromethylcinnamamideYield 75.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To a well stirred solution of 5.0 g of N,N-dimethylcyanoacetamide, 8 ml of triethylamine, and 0.05 g of p-dimethylaminopyridine dissolved in 8 ml of dry THF was added 10 g of 2-nitro-4-trifluoromethylbenzoyl chloride dissolved in a min. amount of THF at such a rate that the reaction temperature did not exceed 45° C. The reaction was stirred overnight, at which time TLC analysis indicated that the reaction was complete. The reaction was worked up by removing the solvents under reduced pressure, diluting the residue with 15% NaOH, and extracting well with ether. The aqueous phase was acidified and extracted with 2×100 ml of CH2Cl2. The combined CH2Cl2 extracts were washed once with saturated brine, dried over molecular sieves, filtered, and then passed through a short column of silica gel. The eluate was concentrated under reduced pressure to yield 9.8 g of an orange oil that solidified upon standing. The impure solid was crystallized from ether/hexane to yield 4.24 g of the product, m.p. 104°-6° C.

Workup

  1. dissolutiondissolved in a min
  2. customdid not exceed 45° C
  3. customby removing the solvents under reduced pressure
  4. additiondiluting the residue with 15% NaOH
  5. extractionextracting well with ether
  6. extractionextracted with 2×100 ml of CH2Cl2
  7. washThe combined CH2Cl2 extracts were washed once with saturated brine
  8. customdried over molecular sieves
  9. filtrationfiltered
  10. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e80d2842071f4725aeead29ec1f4e3a6
Source dataset
uspto-grants-1988_11
Patent number
US04781750

Reaction notes

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