Propionyl chloride → HCID 18176201, compound

HRID 507455Notes

Reaction equation

HRID 507455 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[CH:14]=3)=[N:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[C:20](Cl)(=[O:23])[CH2:21][CH3:22]>C1COCC1>[Br:19][C:15]1[CH:14]=[C:13]([NH:12][C:6]2[C:5]3[C:10](=[CH:11][C:2]([NH:1][C:20](=[O:23])[CH2:21][CH3:22])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 62324Propionyl chlorideHCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline

Product 1

HCID 18176201HCID 18176201, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-amino-4-[(3-bromophenyl)amino]-quinazoline (163 mg, 0.52 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 1 hour the solid was collected by Buchner filtration and washed with ether then dried. Recrystallized from wet methanol afforded the desired product as bright yellow solid (81 mg, 38%), mp 282-283° C.

Workup

  1. customA yellow solid formed at once
  2. filtrationAfter 1 hour the solid was collected by Buchner filtration
  3. washwashed with ether
  4. customthen dried
  5. customRecrystallized from wet methanol

Sources & evidence

ORD record
ord-da59870f25ea4fa39a4b2f3742979a82
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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