Dimethylformamide → HCID 14575317、化合物

HRID 1085686ノート

反応式

HRID 1085686 の反応式
[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

参加物

5

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 11961759HCID 11961759、化合物HCID 14575306HCID 14575306、化合物

生成物 1

HCID 14575317HCID 14575317、化合物収率 49%

反応条件

温度
60 °C

実験手順

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 trichloromthane 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).

後処理

  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 trichloromthane 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

出典と根拠

ORDレコード
ord-577b5faf358d4368b7d01e42ea312e27
出典データセット
uspto-grants-1991_04
特許番号
US05010198

反応ノート

読み込み中…