Water → 4-(2-Chlorophenyl)-9-hydroxy-6-[3-(phenylsulfanyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11101

반응식

HRID 11101 반응식
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:17]2[CH:16]=[C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:14]3[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:13]=3[C:12]=2[C:11]2[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]1=2.[C:31]1([SH:37])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C.O>O1CCOCC1>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[C:14]2[C:25](=[O:29])[NH:26][C:27](=[O:28])[C:13]=2[C:12]2[C:11]3[CH:10]=[C:9]([OH:30])[CH:8]=[CH:7][C:6]=3[N:5]([CH2:4][CH2:3][CH2:2][S:37][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:17]=2[CH:16]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 7969ThiophenolHCID 8471TriethylamineHCID 219805126-(3-Bromopropyl)-4-(2-chlorophenyl)-9-hydroxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

생성물 1

HCID 867602034-(2-Chlorophenyl)-9-hydroxy-6-[3-(phenylsulfanyl)propyl]pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

A solution of the bromide (58) (41 mg, 0.085 mmol) prepared as described in example 172, thiophenol (9.5 μL, 0.093 mmol) and triethylamine (0.25 mL, 3.40 mmol) in p-dioxane (1.5 mL) was refluxed for 16 h. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness the sulfide (131) directly (37.2 mg, 85%), which crystallised from ethyl acetate/petroleum ether as an orange powder, mp 229–231° C. 1H NMR δ [(CD3)2SO] 11.06 (br s, 1H), 9.37 (s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.76 (s, 1H), 7.60–7.42 (m, 5H), 7.25–7.19 (m, 4H), 7.16–7.10 m, 2H), 4.57 (t, J=6.8 Hz, 2H), 2.98 (m, 2H), 2.01 (m, 2H). Found: C, 67.36; H, 4.29; N, 5.36. C29H21ClN2SO3.114H2O requires C, 67.31; H, 4.19; N, 5.41.

후처리

  1. temperaturewas refluxed for 16 h
  2. extractionthe mixture was extracted with ethyl acetate
  3. customThe organic layer was dried
  4. customthe drying agent was removed
  5. concentrationthe solution was concentrated to dryness the sulfide (131) directly (37.2 mg, 85%), which
  6. customcrystallised from ethyl acetate/petroleum ether as an orange powder, mp 229–231° C

출처 및 근거

ORD 기록
ord-d5151d0c90e84864901a4cd4c077061f
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094798B1

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