2-Aminophenol → HCID 13021704, compound

HRID 1009768Notes

Reaction equation

HRID 1009768 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11](O)=O)=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:14](O)=O.[NH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[OH:24].O.[C:26](=[O:29])([O-])[O-].[Na+].[Na+]>>[O:24]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:14]1[C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([C:11]3[O:29][C:26]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[N:17]=3)[CH:6]=2)[CH:1]=1

Participants

4

Reactant 3

HCID 58012-AminophenolHCID 143572,6-Naphthalenedicarboxylic acidHCID 2735133Sodium Carbonate Monohydrate

Product 1

HCID 13021704HCID 13021704, compoundYield 75%

Conditions

Temperature
70 °C

Procedure

Synthesis of 2-(2-(benzo[d]oxazole-2-yl)naphthalene-6-yl)benzo[d]oxazole polyphosphoric acid (125 cm3) was heated at 70° C. for 1 hour while agitating. 0.1 mol of naphthalene-2,6-dicarboxylic acid was added and the resulting mixture was stirred for 15 minutes. 0.2 mol of 2-aminophenol was added in a dropwise fashion for 10 minutes. The temperature of the mixture was increased to 150° C. and then this temperature was maintained for 2 hours. The mixture was stirred to cool down to a room temperature. The resulting reaction mixture was stirred for 1 hour with ice water (1.5 dm3), and neutralized with a diluted sodium carbonate hydrate solution. Then it was filtered and dried in an oven for 1 day. The solid was crystallized from dimethylformamide (200 cm3). The final filtered product was rinsed with methanol (100 cm3) and then dried in a 100° C. vacuum oven. As a result, colorless needle-shaped crystalline 2-(2-(benzo[d]oxazole-2-yl)naphthalene-6-yl) benzo[d]oxazole was produced at a yield of 75%.

Workup

  1. stirringthe resulting mixture was stirred for 15 minutes
  2. temperatureThe temperature of the mixture was increased to 150° C.
  3. temperaturethis temperature was maintained for 2 hours
  4. stirringThe mixture was stirred
  5. temperatureto cool down to a room temperature
  6. customThe resulting reaction mixture
  7. filtrationThen it was filtered
  8. customdried in an oven for 1 day
  9. customThe solid was crystallized from dimethylformamide (200 cm3)
  10. filtrationThe final filtered product
  11. washwas rinsed with methanol (100 cm3)
  12. customdried in a 100° C. vacuum oven

Sources & evidence

ORD record
ord-0fd52d990f624506a70f9f19532f811b
Source dataset
uspto-grants-2011_07
Patent number
US07973168B2

Reaction notes

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