1,1'-Carbonyldiimidazole → 6-chloro-4-(2-phenylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one

HRID 440263ノート

反応式

HRID 440263 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9]([OH:22])([C:14]#[C:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]([F:13])([F:12])[F:11].[C:23](N1C=CN=C1)(N1C=CN=C1)=[O:24]>C1COCC1>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:23](=[O:24])[O:22][C:9]([C:14]#[C:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)([C:10]([F:13])([F:11])[F:12])[C:3]=2[CH:4]=1

参加物

4

反応物 2

HCID 682631,1'-CarbonyldiimidazoleHCID 111209342-(2-Amino-5-chlorophenyl)-4-phenyl-1,1,1-trifluoro-3-butyn-2-ol

生成物 1

HCID 4771206-chloro-4-(2-phenylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one収率 40.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-(2-amino-5-chlorophenyl)-4-phenyl-1,1,1-trifluoro-3-butyn-2-ol (2.0 g, 6.1 mmol) and 11.0 g (12.0 mmol) of 1,1'-carbonyldiimidazole in 300 mL of dry THF was stirred under argon at 55° C. for 24 hours. The solvent was removed on a rotary evaporator and the residue was partitioned between 200 mL of ether and 400 mL of water. The layers were separated and the aqueous extracted once more with ether. The combined ether extracts were washed with 2×200 mL 10% citric acid and then with brine before drying over MgSO4. Removal of the drying agent and solvent provided 1.5 g (70%) of the crude title compound as an oil. Trituration with ether-hexane afforded 875 mg of (±) 6-chloro-4-phenylethynyl-4-trifluoromethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one as a white solid, partial melt at 137°, clear at 147° C. 1H-NMR (CDCl3): δ6.92 (d, J=8 Hz, 1H), 7.30-7.49 (m, 4H), 7.58-7.65 (m, 3H), 8.99 (s, 1H).

後処理

  1. customThe solvent was removed on a rotary evaporator
  2. customthe residue was partitioned between 200 mL of ether and 400 mL of water
  3. customThe layers were separated
  4. extractionthe aqueous extracted once more with ether
  5. washThe combined ether extracts were washed with 2×200 mL 10% citric acid
  6. dry with materialwith brine before drying over MgSO4
  7. customRemoval of the drying agent and solvent
  8. customprovided 1.5 g (70%) of the crude title compound as an oil

出典と根拠

ORDレコード
ord-ef94c9293c684cf7826cf2c74aa6e9dd
出典データセット
uspto-grants-1996_05
特許番号
US05519021

反応ノート

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