trans-Crotonyl chloride → HCID 5328982, compound

HRID 583092Notes

Reaction equation

HRID 583092 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH2:19])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.[C:20](Cl)(=[O:24])/[CH:21]=[CH:22]/[CH3:23]>N1C=CC=CC=1.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([NH:19][C:20](=[O:24])/[CH:21]=[CH:22]/[CH3:23])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

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

Product 1

HCID 5328982HCID 5328982, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.6 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 15 ml of pyridine was cooled in an ice bath and a solution of 0.57 ml of trans-crotonoyl chloride in 6 ml of ether was added dropwise. After stirring and cooling for 2 hours, the solvents were removed at reduced pressure. The residue was treated with water and the resulting solid recrystallized from n-butanol to give 0.69 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-(E)-2-butenamide: mp=153-160° C., mass spectrum (m/e): M+H 383, 385.

Workup

  1. temperaturecooling for 2 hours
  2. customthe solvents were removed at reduced pressure
  3. additionThe residue was treated with water
  4. customthe resulting solid recrystallized from n-butanol

Sources & evidence

ORD record
ord-9820c5c64b2b4a9d80e1a24bc8c10367
Source dataset
uspto-grants-1999_07
Patent number
US05929080

Reaction notes

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