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

HRID 394725ノート

反応式

HRID 394725 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-865809982dde4a86acbf5c0e36b19187
出典データセット
uspto-grants-2003_08
特許番号
US06602863B1

反応ノート

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