Diisopropylethylamine → HCID 66955433, compound

HRID 1948515Notes

Reaction equation

HRID 1948515 reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:12])/[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][CH:5]=1.[C:13]1([C:19]2[C:23]([C:24]([F:27])([F:26])[F:25])=[C:22]([C:28](F)=O)[O:21][N:20]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C>C(#N)C>[C:13]1([C:19]2[C:23]([C:24]([F:26])([F:27])[F:25])=[C:22]([C:28]3[O:1][N:2]=[C:3]([C:4]4[CH:9]=[CH:8][C:7]([CH:10]=[CH2:11])=[CH:6][CH:5]=4)[N:12]=3)[O:21][N:20]=2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 252709594-ethenyl-N'-hydroxybenzenecarboximidamideHCID 58374067HCID 58374067, compound

Product 1

HCID 66955433HCID 66955433, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
62 °C

Procedure

To a mixture of (Z)—N′-hydroxy-4-vinylbenzimidamide (1.439 g, 8.87 mmol) and 3-phenyl-4-(trifluoromethyl)isoxazole-5-carbonyl fluoride (2.300 g, 8.87 mmol) in acetonitrile was added DIEA (1.860 mL, 10.65 mmol). The reaction mixture was heated to 62° C. After 3 hours, the reaction mixture was cooled and a white solid precipitate formed. The solid was filtered and washed with ethyl acetate, then dried to give about 2.1 g of 5-(3-phenyl-4-(trifluoromethyl)isoxazol-5-yl)-3-(4-vinylphenyl)-1,2,4-oxadiazole. MS (m+1)=384. HPLC Peak RT=1.24 minutes (Analytical Method B).

Workup

  1. temperaturethe reaction mixture was cooled
  2. customa white solid precipitate formed
  3. filtrationThe solid was filtered
  4. washwashed with ethyl acetate
  5. customdried

Sources & evidence

ORD record
ord-f2142075fd044b3698f2af9a1ead94ed
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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