Acetic Acid → HCID 13957658, compound

HRID 2308914Notes

Reaction equation

HRID 2308914 reaction equation
C(O)(=O)C.[F:5][C:6]([F:29])([F:28])[C:7]1[NH:8][C:9]([C:24]([F:27])([F:26])[F:25])=[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]([CH3:18])[C:12]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14].N([O-])=O.[Na+]>O>[F:29][C:6]([F:5])([F:28])[C:7]1[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([CH3:18])[C:10]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:9]([C:24]([F:25])([F:27])[F:26])[N:8]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 13957627HCID 13957627, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13957658HCID 13957658, compoundYield 43.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 ml round bottomed flask is charged with 20 ml of glacial acetic acid. To this is added 5 g (0.0133 mole) of diethyl 2,6-bis(trifluoromethyl)-4-methyl-1,4-dihydro-3,5-pyridinedicarboxylate, followed by a slow addition of 3 g (0.0434 mole) of sodium nitrite. The flask is immediately fitted with a condenser and nitrogen line, the stirring continued for 18 hours, and the mixture is poured over crushed ice and water. The organics are extracted twice with ether, washed once with saturated aqueous sodium chloride and washed twice with saturated aqueous sodium bicarbonate solution. The organics are dried over anhydrous magnesium sulfate and concentrated yielding 2.16 g (43.5%) of product, m.p. 55°-58° C.

Workup

  1. customThe flask is immediately fitted with a condenser
  2. additionthe mixture is poured
  3. extractionThe organics are extracted twice with ether
  4. washwashed once with saturated aqueous sodium chloride
  5. washwashed twice with saturated aqueous sodium bicarbonate solution
  6. dry with materialThe organics are dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-58a946a31b104b9e8241b4a145214834
Source dataset
uspto-grants-1987_09
Patent number
US04692184

Reaction notes

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