Sulfuric Acid → HCID 9817543, compound

HRID 1385198Notes

Reaction equation

HRID 1385198 reaction equation
[NH2:1][C:2]1[C:3](=[O:14])[C:4]2[C:9]([C:10](=[O:13])[C:11]=1Cl)=[CH:8][CH:7]=[CH:6][CH:5]=2.[F:15][C:16]1[CH:24]=[CH:23][CH:22]=[CH:21][C:17]=1[C:18](Cl)=[O:19].S(=O)(=O)(O)O.CCOCC>[N+](C1C=CC=CC=1)([O-])=O>[O:14]=[C:3]1[C:2]2[N:1]=[C:18]([C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[F:15])[O:19][C:11]=2[C:10](=[O:13])[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]1=2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 98082-Fluorobenzoyl chlorideHCID 177482-Amino-3-chloro-1,4-naphthoquinone

Product 1

HCID 9817543HCID 9817543, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 7416NitrobenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6.0 g (28.8 mmol) of 2-amino-3-chloro-1,4-dihydro-1,4-dioxonaphthalene in 120 mL of nitrobenzene, 17.10 mL (144.0 mmol) of 2-fluorobenzoic acid chloride are added with protection from light. After 10 min of stirring at 80° C., 0.20 mL of concentrated sulfuric acid is added. The reaction mixture is heated to reflux for 18 h. After complete cooling, ether is added to produce a yellow precipitate, which is filtered through fritted glass and washed with ether. This solid is then purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 60/40) to produce 2.5 g of 4,9-dihydro-4,9-dioxo-2-(2-fluorophenyl)-naphtho[2,3-d]oxazole in the form of yellow crystals.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 18 h
  3. customto produce a yellow precipitate, which
  4. filtrationis filtered through fritted glass
  5. washwashed with ether
  6. customThis solid is then purified on a flash column (support: silica; conditioning: heptane; eluant: dichloromethane/heptane, 60/40)

Sources & evidence

ORD record
ord-d616f13a7cff43249ecc4e9ad088869e
Source dataset
uspto-grants-2001_07
Patent number
US06262095B1

Reaction notes

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