Water → HCID 19832680, compound

HRID 2051093Notes

Reaction equation

HRID 2051093 reaction equation
[H-].[Na+].[F:3][C:4]([F:14])([F:13])/[C:5](/[NH2:12])=[CH:6]/[C:7]([O:9]CC)=O.[CH2:15]([N:17]([CH2:31][CH3:32])[C:18](=[O:30])[C:19]1[CH:24]=[C:23]([N:25]=[C:26]=[O:27])[C:22]([F:28])=[CH:21][C:20]=1[Cl:29])[CH3:16].O>CN(C)C=O.C1(C)C=CC=CC=1.C(O)(=O)C>[CH2:31]([N:17]([CH2:15][CH3:16])[C:18](=[O:30])[C:19]1[CH:24]=[C:23]([N:25]2[C:7](=[O:9])[CH:6]=[C:5]([C:4]([F:3])([F:13])[F:14])[NH:12][C:26]2=[O:27])[C:22]([F:28])=[CH:21][C:20]=1[Cl:29])[CH3:32]

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5702529Ethyl 3-amino-4,4,4-trifluorocrotonateHCID 19832694HCID 19832694, compound

Product 1

HCID 19832680HCID 19832680, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent2×HCID 6228DimethylformamideSolvent2×

Procedure

An 80% suspension of 1.75 g of sodium hydride in refined oil is placed in 20 ml of dimethylformamide and 2.5 ml of toluene. 10.2 g of ethyl 4,4,4-trifluoro-3-aminocrotonate in 50 ml of dimethylformamide are added dropwise to the mixture at 5° to 15° C. and the thus-obtained reaction solution is stirred for 1 hour and subsequently cooled to -50° to -60° C. 12.6 g of N,N-diethyl-2-chloro-4-fluoro-5-isocyanatobenzamide in 25 ml of toluene are then added dropwise thereto and the mixture is stirred at this low temperature for a further 2 hours. Thereafter, the reaction solution is left to stand for about 16 hours, whereby it warms to room temperature. The solution is poured into 1 l of water and the aqueous solution is adjusted to a pH value of 5 with the addition of glacial acetic acid. Subsequently, the solution is extracted twice with 1 l of acetic acid, washed once with 1 l of water and once with 500 ml of saturated sodium chloride solution. The organic phases are combined, dried with anhydrous magnesium sulphate and concentrated. The residue obtained is recrystallized from ethyl acetate. In this manner there is obtained N,N-diethyl-2-chloro-5-[3,6-dihydro-2,6-dioxo-4-trifluoromethyl-1(2H)-pyrimidinyl]-4-fluorobenzamide, m.p. 253°-254° C.

Workup

  1. customthe thus-obtained reaction solution
  2. temperaturesubsequently cooled to -50° to -60° C
  3. stirringthe mixture is stirred at this low temperature for a further 2 hours
  4. waitThereafter, the reaction solution is left
  5. waitto stand for about 16 hours
  6. customwarms to room temperature
  7. extractionSubsequently, the solution is extracted twice with 1 l of acetic acid
  8. washwashed once with 1 l of water and once with 500 ml of saturated sodium chloride solution
  9. dry with materialdried with anhydrous magnesium sulphate
  10. concentrationconcentrated
  11. customThe residue obtained
  12. customis recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-177df99f023a4522ae7b91ccac460b4c
Source dataset
uspto-grants-1991_05
Patent number
US05017211

Reaction notes

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