Acetic Acid → HCID 13957658, compound

HRID 1111071Notes

Reaction equation

HRID 1111071 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-l,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-086edcb71a3f4b8b8fb2f61c7ab29ab8
Source dataset
uspto-grants-1990_12
Patent number
US04978384

Reaction notes

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