Sulfuric Acid → 5-(4-Chlorophenyl-phenylmethyl)-2-pyridone

HRID 1390328

반응식

HRID 1390328 반응식
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6](O)[C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=1.S(=O)(=O)(O)O.C(OCC)(=O)C>O>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:20]2[CH:21]=[CH:22][C:17](=[O:16])[NH:18][CH:19]=2)=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 1118Sulfuric AcidHCID 84014-ChlorobenzhydrolHCID 8857Ethyl AcetateHCID 178516071HCID 178516071, 화합물

생성물 1

HCID 227487995-(4-Chlorophenyl-phenylmethyl)-2-pyridone

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
25 °C

실험 절차

Combine 109.3 g. (0.5 mole) of 4-chlorobenzhydrol with 142.7 g. (1.5 mole) of 2-hydroxypyridine and heat at 150° C. with stirring until molten. Add about 2 ml. of concentrated sulfuric acid and continue heating to 240°-250° C. while removing water from the reaction mixture. Permit the reaction to continue for about 2 hours, then cool the reaction mixture to about 25° C. Treat the resulting solid with ethyl acetate and water and filter to remove the undesired 3-(4-chlorophenyl-phenylmethyl)-2-pyridone. The organic layer is separated and washed with water several times and dried over potassium carbonate and filtered. Concentrate the filtrate to half volume and filter to remove the remaining 3-substituted-2-pyridone. Evaporate the filtrate and dissolve the residue in ethyl ether. Upon standing overnight the 5-(4-chlorophenyl-phenylmethyl)-2-pyridone crystallizes, yield 60 g., m.p. 164°-169° C.

후처리

  1. additionAdd about 2 ml
  2. customwhile removing water from the reaction mixture
  3. customthe reaction
  4. filtrationfilter
  5. customto remove the undesired 3-(4-chlorophenyl-phenylmethyl)-2-pyridone
  6. customThe organic layer is separated
  7. washwashed with water several times
  8. dry with materialdried over potassium carbonate
  9. filtrationfiltered
  10. concentrationConcentrate the filtrate to half volume
  11. filtrationfilter
  12. customto remove the remaining 3-substituted-2-pyridone
  13. customEvaporate the filtrate
  14. dissolutiondissolve the residue in ethyl ether
  15. waitUpon standing overnight
  16. customthe 5-(4-chlorophenyl-phenylmethyl)-2-pyridone crystallizes

출처 및 근거

ORD 기록
ord-072bd13939bc4688af71208be225f59c
출처 데이터셋
uspto-grants-1979_02
특허 번호
US04138488

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