Hydrochloric Acid → 2-Chloro-6-trifluoromethylbenzothiazole

HRID 30891

反応式

HRID 30891 の反応式
Cl[C:2]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=1[NH2:4].[C:13](=[S:18])(OCC)[S-].[K+].[ClH:20]>CN(C=O)C>[Cl:20][C:13]1[S:18][C:2]2[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:3]=2[N:4]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 1620012-Chloro-4-trifluoromethylanilineHCID 2735045Potassium ethylxanthate

生成物 1

HCID 114704192-Chloro-6-trifluoromethylbenzothiazole収率 99%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of 2-chloro-4-trifluoromethylaniline (15.0 g, 76.7 mmol) and potassium O-ethyl dithiocarbonate (29.5 g, 184.1 mmol) in 75 mL anhydrous DMF was heated at 130° C. overnight under a nitrogen atmosphere. The reaction mixture was cooled to rt, and then 1 N HCl solution (200 mL) was added with stirring to induce precipitation. After the mixture was stirred for 30 minutes, the solid precipitate was collected by filtration and rinsed with water. The filter cake was dissolved in 100 mL EtOAc, and the solution was dried over Na2SO4. EtOAc was removed by rotary evaporation, and the residue was dried in vacuo to afford the desired product as a white solid (18.0 g, 99%). 1H NMR (DMSO-d6) δ 14.00 (bs, 1H), 8.20 (s, 1H), 7.70 (d, 1H), 7.40 (d, 1H); GC-EIMS m/z 235 (M+).

後処理

  1. temperatureThe reaction mixture was cooled to rt
  2. customprecipitation
  3. stirringAfter the mixture was stirred for 30 minutes
  4. filtrationthe solid precipitate was collected by filtration
  5. washrinsed with water
  6. dissolutionThe filter cake was dissolved in 100 mL EtOAc
  7. dry with materialthe solution was dried over Na2SO4
  8. customEtOAc was removed by rotary evaporation
  9. customthe residue was dried in vacuo

出典と根拠

ORDレコード
ord-271aedb946a045a0bdfcbdee70c87dee
出典データセット
uspto-grants-2008_09
特許番号
US07423156B2

関連ノート

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