trans-Crotonyl chloride → HCID 5328982, compound

HRID 394744Notes

Reaction equation

HRID 394744 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:24])/[CH:21]=[CH:22]/[CH3:23]>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:24])/[CH:21]=[CH:22]/[CH3:23])[CH:3]=3)[N:8]=[CH:7][N:6]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 643131trans-Crotonyl chlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 5328982HCID 5328982, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-amino-4-[(3-bromophenyl)amino]quinazoline (316 mg, 1.0 mmol) in THF (6 mL) stirred under N2 at 0° C. was added trans-crotonyl chloride. A yellow solid formed upon addition. The solid was collected by Buchner filtration after 2.5 hours and sonicated with EtOAc to give the title compound (216 mg, 52%), mp 279-281° C.

Workup

  1. customA yellow solid formed upon addition
  2. filtrationThe solid was collected by Buchner filtration after 2.5 hours
  3. customsonicated with EtOAc

Sources & evidence

ORD record
ord-f90fa906160e4322933d49ecb7f0a8bd
Source dataset
uspto-grants-2003_08
Patent number
US06602863B1

Reaction notes

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