Dimethylformamide → HCID 14575317, 화합물

HRID 1723436노트

반응식

HRID 1723436 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH2:9][CH2:10][CH2:11][CH2:12]Cl)[CH:3]=1.[CH3:14][N:15]([CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.[C:31](=[O:34])([O-:33])[O-].[Na+].[Na+].CN(C)C=[O:40]>>[C:9]([OH:40])(=[O:8])/[CH:10]=[CH:11]\[C:31]([OH:33])=[O:34].[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][CH2:9][CH2:10][CH2:11][CH2:12][N:28]1[CH2:27][CH2:26][CH:25]([N:15]([CH3:14])[C:16]2[S:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)[CH2:30][CH2:29]1

참가 물질

5

반응물 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11961759HCID 11961759, 화합물HCID 14575306HCID 14575306, 화합물

생성물 1

HCID 14575317HCID 14575317, 화합물수율 49%

반응 조건

온도
60 °C

실험 절차

A mixture of 4.4 parts of 1-chloro-3-(4-chlorobutoxy)benzene, 3.7 parts of N-methyl-N-(4-piperidinyl)-2-benzothiazolamine, 2.1 parts of sodium carbonate and 90 parts of N,N-dimethylformamide was stirred for 24 hours at 60° C. The reaction mixture was cooled and poured onto water. The product was extracted with methylbenzene. The extract was washed with water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (97:3 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was converted into the (Z)-2-butenedioate salt in 2-propanone. The salt was filtered off and dried, yielding 4 parts (49%) of N-[1-[4-(3-chlorophenoxy)butyl]-4-piperidinyl]-N-methyl-2-benzothiazolamine (Z)-2-butenedioate (1:1); mp. 138.6° C. (1).

후처리

  1. temperatureThe reaction mixture was cooled
  2. additionpoured onto water
  3. extractionThe product was extracted with methylbenzene
  4. washThe extract was washed with water
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (97:3 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated
  12. filtrationThe salt was filtered off
  13. customdried

출처 및 근거

ORD 기록
ord-ad8b3ebfc1814be3aa083061ab735b37
출처 데이터셋
uspto-grants-1989_08
특허 번호
US04861785

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