Dichloromethane → 5-Chloro-3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazole

HRID 1870553ノート

反応式

HRID 1870553 の反応式
O.O.Cl.[F:4][C:5]([F:16])([F:15])[C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[NH:11])=[CH:8][CH:7]=1.C(Cl)Cl.[Cl:20][C:21]([SH:24])(Cl)Cl.[OH-].[Na+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:20][C:21]1[S:24][N:12]=[C:10]([C:9]2[CH:13]=[CH:14][C:6]([C:5]([F:15])([F:16])[F:4])=[CH:7][CH:8]=2)[N:11]=1

参加物

7

反応物 4

HCID 6344DichloromethaneHCID 6390TrichloromethanethiolHCID 14798Sodium HydroxideHCID 446307714-(Trifluoromethyl)benzene-1-carboximidamide--hydrogen chloride--water (1/1/2)

生成物 1

HCID 186966075-Chloro-3-[4-(trifluoromethyl)phenyl]-1,2,4-thiadiazole

試薬・触媒・溶媒 2

HCID 66133Benzyl triethylammonium chloride触媒HCID 962Water溶媒2 回

反応条件

温度
0 °C

実験手順

A mixture of 4-(trifluoromethyl)benzamidine hydrochloride dihydrate (5.0 g), water (50 mL), methylene chloride (100 mL), benzyltriethylammonium chloride (0.44 g), and perchloromethyl mercaptan (2.1 mL) was prepared at room temperature and then cooled to 0° C. A solution of sodium hydroxide (3.07 g) in water (50 mL) was added via an addition funnel while maintaining the temperature below 10° C. The reaction was left to stir overnight at room temperature. The mixture was transferred to a separatory funnel and the two layers were separated. The organic layer was washed with saturated sodium bicarbonate, dried (MgSO4), filtered and concentrated under reduced pressure. The crude material was purified by flash chromatography (hexane as eluent) to afford 3.7 g of the title compound of Step H as a white powder. 1H NMR (CDCl3): δ 8.36 (d,2H), 7.73 (d,2H).

後処理

  1. customwas prepared at room temperature
  2. temperaturewhile maintaining the temperature below 10° C
  3. waitThe reaction was left
  4. customThe mixture was transferred to a separatory funnel
  5. customthe two layers were separated
  6. washThe organic layer was washed with saturated sodium bicarbonate
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe crude material was purified by flash chromatography (hexane as eluent)

出典と根拠

ORDレコード
ord-c0a397c955074972910c706290228cb3
出典データセット
uspto-grants-2000_08
特許番号
US06096895

反応ノート

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