Benzoic acid, 2-isothiocyanato-, methyl ester → HCID 14013061, 화합물

HRID 1904850노트

반응식

HRID 1904850 반응식
[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

참가 물질

4

반응물 2

HCID 85243Benzoic acid, 2-isothiocyanato-, methyl esterHCID 14518041HCID 14518041, 화합물

생성물 1

HCID 14013061HCID 14013061, 화합물수율 46%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-521462cd1a7e4356875c565051851635
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04839374

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