3-Methyl-2-butenoyl chloride → HCID 9952643, compound

HRID 430492Notes

Reaction equation

HRID 430492 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.[CH3:20][C:21]([CH3:26])=[CH:22][C:23](Cl)=[O:24]>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:23](=[O:24])[CH:22]=[C:21]([CH3:26])[CH3:20])[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1023943-Methyl-2-butenoyl chlorideHCID 5328042N4-(3-Bromophenyl)quinazoline-4,6-diamine

Product 1

HCID 9952643HCID 9952643, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 1.58 g of N-(3-bromophenyl)-4,6-quinazolindiamine in 15 ml of pyridine was cooled in an ice bath and a solution of 0.67 ml of 3,3-dimethylacryloyl chloride in 7 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 was recrystallized from methyl cellusolve to give 0.97 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-3-methyl-2-butenamide: mp=300-301° C., mass spectrum (m/e): 396, 398.

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 was recrystallized from methyl cellusolve

Sources & evidence

ORD record
ord-66948c43df544a66a8209edb194c81e4
Source dataset
uspto-grants-2001_11
Patent number
US06323209B1

Reaction notes

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