Sulfuric Acid → HCID 22664370, compound

HRID 1281062Notes

Reaction equation

HRID 1281062 reaction equation
[OH-].[Na+].[F:3][C:4]([F:39])([F:38])[C:5]1[CH:6]=[CH:7][C:8]([N+:35]([O-])=O)=[C:9]([N:11]=[N:12][C:13]2[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=3)([CH3:25])[CH3:24])[C:14]=2[OH:34])[CH:10]=1.ClC1C(=O)C2C(C(=O)C=1Cl)=CC=CC=2.S(=O)(=O)(O)O>O.C(O)CCC.CCCCCCC.CC(O)CC>[F:3][C:4]([F:39])([F:38])[C:5]1[CH:6]=[CH:7][C:8]2=[N:35][N:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)([CH3:25])[CH3:24])[C:14]=3[OH:34])[N:11]=[C:9]2[CH:10]=1

Participants

9

Reactant 4

HCID 1118Sulfuric AcidHCID 8342DichloneHCID 14798Sodium HydroxideHCID 135674115HCID 135674115, compound

Product 1

HCID 22664370HCID 22664370, compound

Reagents, catalysts & solvents 4

HCID 2631-ButanolSolventHCID 962WaterSolventHCID 6568(+-)-2-ButanolSolventHCID 8900HeptaneSolvent

Conditions

Temperature
90 °C

Procedure

To a 2 L, five-necked flask equipped with a mechanical stirrer, 500 mL of 2-butanol and 8 g of sodium hydroxide pellets are charged and heated to 90° C. A solution of 50 g of the monoazo compound prepared in Example 12, 2.3 g of 2,3-dichloro-1,4-naphthoquinone and 300 mL of heptane is charged to the hot butanol solution over a three hour period. After the addition is complete, the reaction mass is stirred for an additional hour at reflux. To the reaction mass is then added, 100 mL of water and the pH is adjusted to 2 with 30% aqueous sulfuric acid. The aqueous layer is removed and the organic layer is washed once with 100 mL of saturated sodium chloride solution and twice with water. The desired product is crystallized from the solution yielding the title compound as a light yellow solid melting at 140° C. The structure is verified by 1Hnmr and mass spectroscopy analyses.

Workup

  1. customTo a 2 L, five-necked flask equipped with a mechanical stirrer
  2. additionAfter the addition
  3. temperatureat reflux
  4. additionTo the reaction mass is then added
  5. customThe aqueous layer is removed
  6. washthe organic layer is washed once with 100 mL of saturated sodium chloride solution and twice with water
  7. customThe desired product is crystallized from the solution

Sources & evidence

ORD record
ord-bd33b05ee28b4b93bee96fd8201028b5
Source dataset
uspto-grants-2002_09
Patent number
US06451887B1

Reaction notes

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