Benzoic acid, 2-isothiocyanato-, methyl ester → HCID 14013061、化合物

HRID 1904850ノート

反応式

HRID 1904850 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][CH:19]2[CH2:24][CH2:23][N:22]([CH2:25][CH2:26][NH2:27])[CH2:21][CH2:20]2)=[CH:4][CH:3]=1.[N:28]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[C:37](OC)=[O:38])=[C:29]=[S:30]>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[N:11]=[C:10]2[CH2:18][CH:19]2[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][N:27]3[C:37](=[O:38])[C:32]4[C:31](=[CH:36][CH:35]=[CH:34][CH:33]=4)[NH:28][C:29]3=[S:30])[CH2:23][CH2:24]2)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 85243Benzoic acid, 2-isothiocyanato-, methyl esterHCID 14518041HCID 14518041、化合物

生成物 1

HCID 14013061HCID 14013061、化合物収率 46%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a stirred mixture of 5.5 parts of 4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidineethanamine and 90 parts of tetrahydrofuran was added dropwise a solution of 3.8 parts of methyl 2-isothiocyanatobenzenecarboxylate in 18 parts of tetrahydrofuran (exothermic reaction). Upon completion, stirring was continued for 1 hour. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol, saturated with ammonia, (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated. The residue was crystallized from acetonitrile. The product was filtered off and recrystallized from methanol. The product was filtered off and dried, yielding 3.6 parts (46%) of 3-[2-[4-[[1-[(4-fluorophenyl)methyl]-1H-benzimidazol-2-yl]methyl]-1-piperidinyl]ethyl]-2,3-dihydro-2-thioxo-4(1H)-quinazolinone; mp. 218.2° C. (460).

後処理

  1. customThe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel using
  3. additiona mixture of trichloromethane and methanol
  4. customThe pure fractions were collected
  5. customthe eluent was evaporated
  6. customThe residue was crystallized from acetonitrile
  7. filtrationThe product was filtered off
  8. customrecrystallized from methanol
  9. filtrationThe product was filtered off
  10. customdried

出典と根拠

ORDレコード
ord-521462cd1a7e4356875c565051851635
出典データセット
uspto-grants-1989_06
特許番号
US04839374

反応ノート

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