Hydrochloric Acid → HCID 178432088、化合物

HRID 13651

反応式

HRID 13651 の反応式
[CH3:1][S:2]([CH2:5][C:6](=[O:8])[CH3:7])(=[O:4])=[O:3].[Br:9][C:10]1[CH:11]=C[C:13]2[N:18]=[C:17]([CH3:19])OC(=O)[C:14]=2[CH:21]=1.Cl>CN(C)C=O>[Br:9][C:10]1[CH:11]=[C:7]2[C:13](=[CH:14][CH:21]=1)[N:18]=[C:17]([CH3:19])[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[C:6]2[OH:8]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 786951-(Methylsulphonyl)acetoneHCID 27971426-Bromo-2-methyl-4H-3,1-benzoxazin-4-one

生成物 1

HCID 178432088HCID 178432088、化合物収率 48.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Methanesulfonylacetone (12.6 g, 92.9 mmol) was dissolved in N,N-dimethylformamide (200 mL) and cooled in ice under nitrogen. Then potassium tert.butylate (11.7 g, 102 mmol) was added (exothermic 20° C.) and stirring without cooling continued for 15 min. Cooled in ice again, then 6-bromo-2-methyl-4H-3,1-benzoxazin-4-one (example B.1) (22.3 g, 92.9 mmol) was added and then stirred without cooling for 4 h. Cooled in ice again, then potassium tert.butylate (11.7 g, 102 mmol) was added, and the resulting red solution was stirred at 20° C. for 15 min and then heated at 100° C. for 30 min. After cooling, 4 M HCl (30 mL) was added, and the mixture was evaporated thoroughly at 0.1 mbar/50° C. The residue was suspended in water (200 mL) and stirred vigorously for 30 min which led to the formation of a filterable precipitate. This solid was filtered off and washed with water (50 mL). One obtained 14.25 g (48.5%) of white crystals. MS: m/z=315/317 (M+H).

後処理

  1. temperaturecooled in ice under nitrogen
  2. temperaturewithout cooling
  3. temperatureCooled in ice again
  4. stirringstirred
  5. temperaturewithout cooling for 4 h
  6. temperatureCooled in ice again
  7. stirringthe resulting red solution was stirred at 20° C. for 15 min
  8. temperatureAfter cooling
  9. customthe mixture was evaporated thoroughly at 0.1 mbar/50° C
  10. stirringstirred vigorously for 30 min which
  11. filtrationThis solid was filtered off
  12. washwashed with water (50 mL)

出典と根拠

ORDレコード
ord-763ded09876248a7a5b117b5c60294bc
出典データセット
uspto-grants-2010_06
特許番号
US07728142B2

関連ノート

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