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

HRID 11101

Reaction equation

HRID 11101 reaction equation
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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d5151d0c90e84864901a4cd4c077061f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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