trans-Crotonyl chloride → N-[4-(3-Bromoanilino)quinazolin-7-yl]but-2-enamide

HRID 507448Notes

Reaction equation

HRID 507448 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:24])/[CH:21]=[CH:22]/[CH3:23]>O1CCCC1>[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:24])[CH:21]=[CH:22][CH3:23])=[CH:3][CH:4]=3)[N:9]=[CH:8][N:7]=2)[CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 643131trans-Crotonyl chlorideHCID 53280457-Amino-4-[(3-bromophenyl)amino]quinazoline

Product 1

HCID 57101720N-[4-(3-Bromoanilino)quinazolin-7-yl]but-2-enamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice cold solution of 0.158 g of 7-amino-4-(3-bromoanilino)-quinazoline (J Med Chem, 1985:3482) in 5 mL of tetrahydrofuran was added dropwise a solution of 0.105 g of crotonic acid chloride in 5 mL of tetrahydrofuran. When the addition was complete, the ice bath was removed and the reaction stirred at room temperature for 15 hours. The reaction was filtered to remove the yellow solid which was washed with tetrahydrofuran and recrystallized from 20 mL of boiling methanol to afford 0.060 g of the desired product, mp >250° C.

Workup

  1. additionWhen the addition
  2. customthe ice bath was removed
  3. filtrationThe reaction was filtered
  4. customto remove the yellow solid which
  5. washwas washed with tetrahydrofuran
  6. customrecrystallized from 20 mL of boiling methanol

Sources & evidence

ORD record
ord-df6f0f96925a49a999fb08487a8cda9e
Source dataset
uspto-grants-2010_08
Patent number
US07786131B2

Reaction notes

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