Hydrochloric Acid → 2-Chloro-6-trifluoromethylbenzothiazole

HRID 30891

반응식

HRID 30891 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 114704192-Chloro-6-trifluoromethylbenzothiazole수율 99%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-271aedb946a045a0bdfcbdee70c87dee
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423156B2

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