Formaldehyde → 1H-Benzotriazole-1-methanol

HRID 445027

반응식

HRID 445027 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[CH2:9]=[O:10].[NH:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1>>[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH:5][CH3:14].[OH:10][CH2:9][N:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[N:13]=[N:12]1.[NH:11]1[C:3]2[CH:2]=[CH:8][CH:7]=[CH:6][C:4]=2[N:5]=[N:12]1

참가 물질

6

반응물 3

HCID 712FormaldehydeHCID 97423-FluoroanilineHCID 178418385HCID 178418385, 화합물

생성물 3

HCID 2241691H-Benzotriazole-1-methanolHCID 27590113-fluoro-N-methylanilineHCID 178418385HCID 178418385, 화합물

실험 절차

3-Fluoro-N-methylaniline was prepared from 3-fluoroaniline using a modified reductive amination. First, 1-hydroxymethylbenzotriazole was prepared by adding 37% aqueous formaldehyde to benzotriazole at 40° C. in a 1:1 ratio, then cooling to room temperature to precipitate the product. After filtration the hydroxymethylbenzotriazole (125 g) was heated to reflux in toluene with 3-fluoroaniline (92.2 g). Water was removed azeotropically using a Dean-Stark trap. After three hours, the mixture was cooled to room temperature, then refrigerated for several hours to complete precipitation. The white crystalline solid was filtered off, yielding 174.2 g (86.6%) of 1-(3-fluoroanilino)methyl)-1H-benzotriazole.

후처리

  1. customto precipitate the product
  2. filtrationAfter filtration the hydroxymethylbenzotriazole (125 g)
  3. temperaturewas heated
  4. temperatureto reflux in toluene with 3-fluoroaniline (92.2 g)
  5. customWater was removed azeotropically
  6. temperaturethe mixture was cooled to room temperature
  7. waitrefrigerated for several hours
  8. customprecipitation
  9. filtrationThe white crystalline solid was filtered off

출처 및 근거

ORD 기록
ord-402c8ecf220345ff962273731d26bd5e
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476280B2

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