Hydrochloric Acid → 2-Chloro-6-trifluoromethylbenzothiazole

HRID 9576

반응식

HRID 9576 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

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, 1 H), 8.20 (s, 1 H), 7.70 (d, 1 H), 7.40 (d, 1 H); GC-EIMS m/z 235 (M+).

후처리

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

출처 및 근거

ORD 기록
ord-d6e11d08e1fd40d8a5547054fc45b562
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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