Potassium Iodide → Tyclopyrazoflor

HRID 55744

反応式

HRID 55744 の反応式
[H-].[Na+].[Cl:3][C:4]1[C:8]([NH:9][C:10](=[O:20])[CH2:11][CH2:12][S:13][CH2:14][CH2:15][C:16]([F:19])([F:18])[F:17])=[CH:7][N:6]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:5]=1.[CH2:27](Br)[CH3:28].[I-].[K+]>S1(CCCC1)(=O)=O>[Cl:3][C:4]1[C:8]([N:9]([CH2:27][CH3:28])[C:10](=[O:20])[CH2:11][CH2:12][S:13][CH2:14][CH2:15][C:16]([F:18])([F:17])[F:19])=[CH:7][N:6]([C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)[N:5]=1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 86700584N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((3,3,3-trifluoropropyl)thio)propanamide

生成物 1

HCID 86700627Tyclopyrazoflor

試薬・触媒・溶媒 1

HCID 31347Sulfolane溶媒2 回

実験手順

To 3-neck round bottomed flask (50 mL) was added sodium hydride (60% in oil, 0.130 g, 3.28 mmol) and sulfolane (16 mL). The gray suspension was stirred for 5 minutes then N-(3-chloro-1-(pyridin-3-yl)-1H-pyrazol-4-yl)-3-((3,3,3-trifluoropropyl)thio)propanamide (1.20 g, 3.16 mmol) dissolved in sulfolane (25 mL) was slowly added dropwise over 5 minutes. The mixture became a light gray suspension after 3 minutes and was allowed to stir for 5 minutes after which time ethyl bromide (0.800 mL, 10.7 mmol) and potassium iodide (0.120 g, 0.720 mmol) were added sequentially. The cloudy suspension was then allowed to stir at room temperature. The reaction was quenched after 6 hours by being poured drop-wise into cooled ammonium formate/acetonitrile solution (30 mL). The resulting orange colored solution was stirred and tetrahydrofuran (40 mL) was added. The mixture was assayed, using octanophenone as a standard, and found to contain (1.09 g, 85%) of the desired product with a selectivity versus the retro-Michael-like decomposition product of 97:3.

後処理

  1. additionwas slowly added dropwise over 5 minutes
  2. customafter 3 minutes
  3. additionwere added sequentially
  4. stirringto stir at room temperature
  5. customThe reaction was quenched after 6 hours
  6. additionby being poured drop-wise
  7. temperatureinto cooled ammonium formate/acetonitrile solution (30 mL)
  8. stirringThe resulting orange colored solution was stirred
  9. additiontetrahydrofuran (40 mL) was added

出典と根拠

ORDレコード
ord-8c178e7cd78948a2aefcc4ac48964a1b
出典データセット
uspto-grants-2016_09
特許番号
US09433215B2

関連ノート

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