Triethylamine → HCID 178423541、化合物

HRID 471371ノート

反応式

HRID 471371 の反応式
[CH3:1][C:2]1[CH:10]=[C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:28])[F:27])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[CH:17]=3)[O:13][N:12]=2)[CH:8]=[CH:7][C:3]=1[CH:4]=[N:5][OH:6].ClN1C(=O)CCC1=O.[NH2:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[O:41].C(N(CC)CC)C>CN(C=O)C.C1COCC1>[OH:6][N:5]=[C:4]([NH:38][CH2:39][C:40]([NH:42][CH2:43][C:44]([F:47])([F:46])[F:45])=[O:41])[C:3]1[CH:7]=[CH:8][C:9]([C:11]2[CH2:15][C:14]([C:26]([F:29])([F:27])[F:28])([C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([C:22]([F:24])([F:25])[F:23])[CH:17]=3)[O:13][N:12]=2)=[CH:10][C:2]=1[CH3:1]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 31398ChlorosuccinimideHCID 247051432-Amino-N-(2,2,2-trifluoroethyl)acetamideHCID 1371957342-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime

生成物 1

HCID 178423541HCID 178423541、化合物収率 43%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
75 °C

実験手順

To a solution of 2-Methyl-4-[5-trifluoromethyl-5-(3-trifluoromethyl-phenyl)-4,5-dihydro-isoxazol-3-yl]-benzaldehyde oxime (250 mg) in DMF (8 mL) was added N-chloro succinimide (84 mg) and heated to 75° C. for 1 h. After cooling, the reaction mixture was poured onto water and extracted with EtOAc. The combined organic layers were dried (Na2SO4) and concentrated in vacuo to ¼ of the original volume to obtain the crude hydroxamic acid chloride. This mixture was added to a solution of 2-amino-N-(2,2,2-trifluoro-ethyl)-acetamide (116 mg) and triethylamine (0.30 mL, 0.21 g) in THF (8 mL) and stirred at room temperature over night. After concentration in vacuo, the mixture was purified by chromatography on silica gel to obtain the title compound (146 mg, 43%).

後処理

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured onto water
  3. extractionextracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto obtain the crude hydroxamic acid chloride
  7. concentrationAfter concentration in vacuo
  8. customthe mixture was purified by chromatography on silica gel

出典と根拠

ORDレコード
ord-a6e347dba44d4beabc58fc6a6665a1f4
出典データセット
uspto-grants-2014_01
特許番号
US08633134B2

反応ノート

読み込み中…