Diisopropylethylamine → N-[1-cyano-1-methyl-2-(5-cyano-2-{2,4-dichlorophenoxy}-phenoxy)-ethyl]-4-trifluoromethoxybenzamide

HRID 646197Notes

Reaction equation

HRID 646197 reaction equation
[NH2:1][C:2]([C:23]#[N:24])([CH3:22])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])[C:8]#[N:9].C(N(C(C)C)C(C)C)C.[F:34][C:35]([F:47])([F:46])[O:36][C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1>ClCCl>[C:23]([C:2]([NH:1][C:41](=[O:42])[C:40]1[CH:44]=[CH:45][C:37]([O:36][C:35]([F:34])([F:46])[F:47])=[CH:38][CH:39]=1)([CH3:22])[CH2:3][O:4][C:5]1[CH:6]=[C:7]([C:8]#[N:9])[CH:10]=[CH:11][C:12]=1[O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Cl:21])#[N:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1421104-(Trifluoromethoxy)benzoyl ChlorideHCID 686162113-(2-Amino-2-cyano-1-propoxy)-4-(2,4-dichlorophenoxy)-benzonitrile

Product 1

HCID 11214981N-[1-cyano-1-methyl-2-(5-cyano-2-{2,4-dichlorophenoxy}-phenoxy)-ethyl]-4-trifluoromethoxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

13.04 g of 3-(2-amino-2-cyano-1-propoxy)-4-(2,4-dichlorophenoxy)-benzonitrile and 6.1 g of ethyldiisopropylamine are dissolved in 120 ml of dichloromethane. After cooling the mixture to 0°, 9.9 g of 4-trifluoromethoxybenzoyl chloride is added, the reaction mixture stirred at room temperature for 6 h and then concentrated under vacuum. The residue is dissolved in ethylacetate and washed with a 1N aqueous solution of sodium hydroxide, water, a 1N aqueous solution of hydrogen chloride, again with water and finally with brine. The organic phase is dried over magnesium sulfate, filtered and evaporated. The raw residue is then recrystallized in diethylether/hexane, thus yielding the title compound with a melting point of 151-2°.

Workup

  1. temperatureAfter cooling the mixture to 0°
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue is dissolved in ethylacetate
  4. washwashed with a 1N aqueous solution of sodium hydroxide, water
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe raw residue is then recrystallized in diethylether/hexane

Sources & evidence

ORD record
ord-2ba926e6ebaf44b4a16d40a205666a8c
Source dataset
uspto-grants-2010_04
Patent number
US07705047B2

Reaction notes

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