Triethylamine → HCID 15462811, compound

HRID 1636444Notes

Reaction equation

HRID 1636444 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23]>C1COCC1>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6]([C:7]2[O:8][C:22](=[O:23])[NH:10][N:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 5206624-(Trifluoromethyl)benzohydrazide

Product 1

HCID 15462811HCID 15462811, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
24 °C

Procedure

4-(Trifluoromethyl)benzoic acid hydrazide (commercially available from Maybridge Chemicals) (5 g, 24.5 mmol) was taken up in THF (250 ml)/triethylamine (2.7 ml, 26 mmol) under N2 and 1,1'-carbonyl-diimidazole (4.2 g, 26 mmol) added. The solution was stirred for 18 h at 24° C., concentrated, and the residue was taken up in ethyl acetate, washed with 1N HCl solution, sat'd NaHCO3 solution, and brine prior to drying (MgSO4). Concentration gave 5 g (89%) of the title compound from which a sample was recrystallized from diethyl ether/hexanes: mp 214-216° C. MS m/z: 231 (MH+).

Workup

  1. concentrationconcentrated
  2. washwashed with 1N HCl solution
  3. dry with materialto drying (MgSO4)
  4. concentrationConcentration

Sources & evidence

ORD record
ord-9c29c1e79dfd4f8fbe937f523d661f4f
Source dataset
uspto-grants-2000_03
Patent number
US06034113

Reaction notes

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