Propionyl chloride → HCID 4709, compound

HRID 507464Notes

Reaction equation

HRID 507464 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[C:5]2[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C1COCC1>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:1][C:20](=[O:23])[CH2:21][CH3:22])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 4709HCID 4709, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)amino]quinazoline (157 mg, 0.5 mmol) in dry THF (3 mL) stirred under N2 at 25° C. was added dropwise propionyl chloride (0.05 mL, 0.58 mmol). A yellow solid formed at once. After 45 minutes the solid was collected by filtration and washed with ether and dried. Recrystallized from wet methanol afforded the desired product (97 mg, 47%), mp 265-266° C.

Workup

  1. customA yellow solid formed at once
  2. filtrationAfter 45 minutes the solid was collected by filtration
  3. washwashed with ether
  4. customdried
  5. customRecrystallized from wet methanol

Sources & evidence

ORD record
ord-0f41045ceb8e401fad61f2acbb790a06
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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