Hydrochloric Acid → HCID 18184406, compound

HRID 1489582Notes

Reaction equation

HRID 1489582 reaction equation
Cl[C:2]1[C:11]2[N:10]=[CH:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]2[O:12][CH:13]=[N:14][C:3]=12.[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].Cl>C1COCC1.CC(O)C>[Br:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH:19][C:2]1[C:11]2[N:10]=[CH:9][N:8]=[CH:7][C:6]=2[CH:5]=[C:4]2[O:12][CH:13]=[N:14][C:3]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 115623-BromoanilineHCID 18184384HCID 18184384, compound

Product 1

HCID 18184406HCID 18184406, compoundYield 45.5%

Reagents, catalysts & solvents 1

HCID 22597222Tetrahydrofuran 2-propanolSolvent

Procedure

A mixture of 4-chlorooxazolo[5,4-g]quinazoline (0.24 g, 1.16 mmol) and 3-bromoaniline (0.25 mL, 2.33 mmol) in a THF/propan-2-ol mixture (1:1, 40 mL) containing a trace of concentrated HCl is heated under reflux for 15 min, then concentration to dryness under reduced pressure. The residue is triturated with EtOAc, and then partitioned between saturated aqueous NaHCO3 and EtOAc. Workup of the organic portion gives 4-(3-bromoanilino)oxazolo[5,4-g]quinazoline (0.18 g, 33%) as a yellow powder, mp (MeOH) 232 ° C. (dec.).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 15 min
  3. concentrationconcentration to dryness under reduced pressure
  4. customThe residue is triturated with EtOAc
  5. custompartitioned between saturated aqueous NaHCO3 and EtOAc

Sources & evidence

ORD record
ord-17a7bb22b38543a1ad8193a76250bf62
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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