Triethylamine → Trifludimoxazin

HRID 1506580ノート

反応式

HRID 1506580 の反応式
CNC(NC)=[S:4].C(N(CC)CC)C.[F:14][C:15]1([F:33])[O:20][C:19]2[CH:21]=[C:22]([F:28])[C:23]([N:25]=[C:26]=[O:27])=[CH:24][C:18]=2[N:17]([CH2:29][C:30]#[CH:31])[C:16]1=[O:32].[C:34](N1C=CN=C1)([N:36]1[CH:40]=[CH:39][N:38]=[CH:37]1)=[O:35]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:39][N:38]1[C:37](=[S:4])[N:36]([CH3:40])[C:34](=[O:35])[N:25]([C:23]2[C:22]([F:28])=[CH:21][C:19]3[O:20][C:15]([F:14])([F:33])[C:16](=[O:32])[N:17]([CH2:29][C:30]#[CH:31])[C:18]=3[CH:24]=2)[C:26]1=[O:27]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2723631N,N'-DimethylthioureaHCID 866643002,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

生成物 1

HCID 49831143Trifludimoxazin

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒2 回HCID 22728543Water ethylacetate溶媒

反応条件

温度
80 °C

実験手順

To 1,3-dimethylthiourea (2.489 g, 23.89 mmol) and triethylamine (2.78 ml, 19.91 mmol) in dry toluene was added 2,2,7-trifluoro-6-isocyanato-4-(prop-2-ynyl)-2H-benzo[b][1,4]oxazin-3(4H)-one (5.62 g, 19.91 mmol) in dry toluene. Hereto was subsequently added carbonyldiimidazole (CDI; 6.46 g, 39.8 mmol) and the resulting mixture was stirred at 80° C. overnight. Then the reaction mixture was cooled to room temperature and poured into ethyl acetate/water under stirring. The layers were separated and the aqueous layer was extracted with dichloromethane. The combined extracts were washed with brine, dried with Na2SO4 and concentrated to yield 14.4 g.

後処理

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. stirringunder stirring
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washThe combined extracts were washed with brine
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated
  8. customto yield 14.4 g

出典と根拠

ORDレコード
ord-dfb72ae00ef943478f1fcfe7479c35ba
出典データセット
uspto-grants-2015_12
特許番号
US09220268B2

反応ノート

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