p-Toluenesulfonic acid → HCID 22618292, compound

HRID 842109Notes

Reaction equation

HRID 842109 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][CH:20]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[C:9]=1[OH:17])=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(OC2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:17][C:9]3[C:10]([N+:14]([O-:16])=[O:15])=[CH:11][CH:12]=[CH:13][C:8]=3[N:7]=2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7583Diphenyl EtherHCID 22618284HCID 22618284, compound

Product 1

HCID 22618292HCID 22618292, compoundYield 102.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
190 °C

Procedure

A stirred suspension of N-(3-chlorobenzoyl)-2-hydroxy-3-nitroaniline (4.5 g, 0.0117 mol), p-toluenesulfonic acid (0.30 g) and 50 ml of diphenyl ether were heated at 190° C. for 1 hour. The dark reaction mixture was dissolved in 100 ml CH2Cl2 and washed with saturated sodium bicarbonate and then water. The CH2Cl2 was evaporated and hexane was added, causing a brown solid to separate. The dark solid was filtered, dissolved in 75% CH2Cl2 in hexane and washed onto a silica gel column. Elution with this solvent, gave 3.3 g of the title compound. This material could be recrystallized from methanol to give 2-(3-chlorophenyl)-7-nitrobenzoxazole although it was pure enough from the chromatography to use for the next step without any further purification.

Workup

  1. customThe dark reaction mixture
  2. washwashed with saturated sodium bicarbonate
  3. customThe CH2Cl2 was evaporated
  4. additionhexane was added
  5. customto separate
  6. filtrationThe dark solid was filtered
  7. dissolutiondissolved in 75% CH2Cl2 in hexane
  8. washwashed onto a silica gel column
  9. washElution with this solvent

Sources & evidence

ORD record
ord-73e8bc63fd4d4455a69949e873bd4847
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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