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4-Nitrophenyl benzo[d]thiazol-2-ylcarbamate → ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

HRID 1896571
ノート
印刷プレビュー

反応式

HRID 1896571 の反応式
[O:1]1[CH2:6][CH2:5][NH:4][C:3]2[CH:7]=[C:8]([C:11]3[S:12][C:13]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)[CH:9]=[CH:10][C:2]1=2.[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][C:42](=O)[O:43]C1C=CC([N+]([O-])=O)=CC=1>C(#N)C>[S:32]1[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=2[N:34]=[C:33]1[NH:41][C:42]([N:4]1[CH2:5][CH2:6][O:1][C:2]2[CH:10]=[CH:9][C:8]([C:11]3[S:12][C:13]([N:21]([CH3:31])[CH2:22][CH2:23][O:24][C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=4)=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:15]=3)=[CH:7][C:3]1=2)=[O:43]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 594186764-Nitrophenyl benzo[d]thiazol-2-ylcarbamateHCID 59418724ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

生成物 1

HCID 59418665ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate収率 310.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

To ethyl 2-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20B) (0.150 g, 0.34 mmol) and 4-nitrophenyl benzo[d]thiazol-2-ylcarbamate (19) (0.349 g, 0.11 mmol) was added acetonitrile (10 mL). The reaction mixture was allowed to heat to 85° C. and stirred for 8 hours. Then the reaction mixture was allowed to heat at 70° C. and stirred overnight. The reaction mixture was allowed to cool to rt and concentrated under reduced pressure. To the concentrate was added EtOAc and water and filtered. The layers of the filtrate were separated and extracted with EtOAc. The combined organic extracts were washed sequentially with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure to provide 0.21 g (quantitative) ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20C): LC/MS (APCI): m/z 616.3 (M+H).

後処理

  1. temperatureto heat at 70° C.
  2. stirringstirred overnight
  3. temperatureto cool to rt
  4. concentrationconcentrated under reduced pressure
  5. additionTo the concentrate was added EtOAc and water
  6. filtrationfiltered
  7. customThe layers of the filtrate were separated
  8. extractionextracted with EtOAc
  9. washThe combined organic extracts were washed sequentially with water, brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-cdda43c777dc46b5a82138068cfea14b
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08518970B2

反応ノート

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