Diisopropylamine → HCID 53238880, compound

HRID 410124Notes

Reaction equation

HRID 410124 reaction equation
[NH2:1][C:2]([C:27]#[N:28])([CH3:26])[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]([O:20][C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=1[Cl:25])[C:8]#[N:9].C(NC(C)C)(C)C.[F:36][C:37]([F:49])([F:48])[S:38][C:39]1[CH:47]=[CH:46][C:42]([C:43](Cl)=[O:44])=[CH:41][CH:40]=1>ClCCl>[C:27]([C:2]([NH:1][C:43](=[O:44])[C:42]1[CH:46]=[CH:47][C:39]([S:38][C:37]([F:49])([F:36])[F:48])=[CH:40][CH:41]=1)([CH3:26])[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]([O:20][C:21]([F:23])([F:24])[F:22])=[CH:16][C:15]=1[Cl:25])#[N:28]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 27778654-(Trifluoromethylthio)benzoyl chlorideHCID 673925753-(2-Amino-2-cyano-2-methyl-ethoxy)-4-(2-chloro-4-trifluoromethoxy-phenoxy)-benzonitrile

Product 1

HCID 53238880HCID 53238880, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

21.5 g of 3-(2-amino-2-cyano-2-methyl-ethoxy)-4-(2-chloro-4-trifluoromethoxy-phenoxy)-benzonitrile (described in example 1 step d)) and 11.4 ml of N, N-diisopropylamine are dissolved in 250 ml of dichloromethane and 14.5 g of 4-(trifluoromethylthio)-benzoylchloride are slowly added. The reaction mixture is stirred at room temperature for 20 hours and washed with water, a saturated aqueous solution of sodium bicarbonate and water. The organic phase is dried with magnesium sulfate and evaporated under vacuum. The residue is purified by recrystallization from diethylether/hexanes to yield N-[1-cyano-1-methyl-2-(5-cyano-2-{2-chloro-4-trifluoromethoxy-phenoxy}-phenoxy)-ethyl]-4-trifluoromethylsulfanyl-benzamide as a colorless solid.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase is dried with magnesium sulfate
  3. customevaporated under vacuum
  4. customThe residue is purified by recrystallization from diethylether/hexanes

Sources & evidence

ORD record
ord-b877c419057440a694e2d4c594fc5970
Source dataset
uspto-grants-2014_06
Patent number
US08759564B2

Reaction notes

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