Hydrochloric Acid → HCID 18184406, compound

HRID 1358265Notes

Reaction equation

HRID 1358265 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-4bd9d1a7a31446a0b4336bf0799b84a7
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

Loading…