Toluene → Sertaconazole

HRID 1171918

반응식

HRID 1171918 반응식
C1(C)C=CC=CC=1.[Cl:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=1[CH:16]([OH:23])[CH2:17][N:18]1[CH:22]=[CH:21][N:20]=[CH:19]1.[OH-].[Na+].Br[CH2:27][C:28]1[C:29]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:30]=2[S:31][CH:32]=1>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH:35]1[CH:34]=[C:33]([Cl:37])[C:30]2[S:31][CH:32]=[C:28]([CH2:27][O:23][CH:16]([C:10]3[CH:11]=[CH:12][C:13]([Cl:15])=[CH:14][C:9]=3[Cl:8])[CH2:17][N:18]3[CH:19]=[N:20][CH:21]=[CH:22]3)[C:29]=2[CH:36]=1

참가 물질

7

반응물 4

HCID 1140Toluene2회HCID 14798Sodium HydroxideHCID 32238(+-)-alpha-(2,4-Dichlorophenyl)-1H-imidazole-1-ethanolHCID 113799883-(Bromomethyl)-7-chloro-1-benzothiophene

생성물 1

HCID 65863Sertaconazole수율 105.5%

시약·촉매·용매 2

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962Water용매

반응 조건

온도
37.5 °C

실험 절차

A 2-L flask was loaded with 308 mL of toluene, 100 g of 1-(2,4-dichlorophenyl)-2-(1H-imidazol-1-yl)-ethanol (II) (0.389 mol) and 6.67 g of tetrabutylammonium hydrogen sulfate (IV, Z═HSO4) (0.0196 mol). Then, 155 g of sodium hydroxide (purity 49%; 1.905 mol) were added. The mixture was heated at 35-40° C. and stirred for 15 minutes. A solution comprising 111.11 g of 3-bromomethyl-7-chlorobenzo[b]thiophene (III) (0.425 mol) and 595 mL of toluene, maintaining the mass temperature between 37 and 40° C., was added for at least 30 minutes. After the addition, the system was maintained between 37 and 40° C. for 2.5 hours and thereafter water (635 mL) was added. The mixture was cooled to a mass temperature of 5-10° C. and the sertaconazole precipitated was filtered and washed with water and cold toluene (5-10° C.), obtaining 179.7 g of wet sertaconazole free base (161.7 g dry).

후처리

  1. temperaturemaintaining the mass temperature between 37 and 40° C.
  2. additionwas added for at least 30 minutes
  3. additionAfter the addition
  4. temperaturethe system was maintained between 37 and 40° C. for 2.5 hours
  5. temperatureThe mixture was cooled to a mass temperature of 5-10° C.
  6. customthe sertaconazole precipitated
  7. filtrationwas filtered
  8. washwashed with water and cold toluene (5-10° C.)

출처 및 근거

ORD 기록
ord-f065bb089495476c8ec803c540f15c01
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829726B2

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