Thiophenol → HCID 21980573, compound

HRID 11098Notes

Reaction equation

HRID 11098 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[C:20]2[CH:19]=[C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[C:17]3[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:16]=3[C:15]=2[C:14]2[CH:13]=[C:12]([OH:33])[CH:11]=[CH:10][C:9]1=2)(=O)=O.[C:34]1([SH:40])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C>O>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:18]1[C:17]2[C:28](=[O:32])[NH:29][C:30](=[O:31])[C:16]=2[C:15]2[C:14]3[CH:13]=[C:12]([OH:33])[CH:11]=[CH:10][C:9]=3[N:8]([CH2:7][CH2:6][S:40][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8471TriethylamineHCID 100740852-(4-(2-Chlorophenyl)-9-hydroxy-1,3-dioxo-2,3-dihydropyrrolo[3,4-c]carbazol-6 (1H)-yl)ethyl methanesulfonate

Product 1

HCID 21980573HCID 21980573, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

Mesylate (229) (55 mg, 0.11 mmol) prepared as decribed in example 171 was reacted with excess thiophenol (0.10 mL) according to the procedure described in example 179, except that triethylamine (2.0 mL) was added and the reaction was heated at 110° C. for 4 days. Addition of water was followed by extracted of the compound with with ethyl acetate. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness. The organic layer was dried, the drying agent was removed and the solution was concentrated to dryness followed by chromatography on silica eluting with ethyl acetate/hexane (1:4 to 1:1) to give carbazole (242) (16 mg, 27%) as an orange powder, mp 262–264° C. 1H NMR δ [(CD3)2SO] 11.04 (br s, 1H), 9.37 (br s, 1H), 8.34 (d, J=2.5 Hz, 1H), 7.58 (m, 1H), 7.46 (m, 5H), 7.19 (m, 2H), 7.12 (m, 3H), 7.05 (m, 1H), 4.66 (t, J=6.4 Hz, 2H), 3.46 (t, J=6.4 Hz, 2H). Found: C, 63.64; H, 4.09; N, 4.98. C28H19ClN2O3S.1¾H2O requires: C, 63.39; H, 4.28; N, 5.28.

Workup

  1. additionwas added
  2. extractionby extracted of the compound with with ethyl acetate
  3. customThe organic layer was dried
  4. customthe drying agent was removed
  5. concentrationthe solution was concentrated to dryness
  6. customThe organic layer was dried
  7. customthe drying agent was removed
  8. concentrationthe solution was concentrated to dryness

Sources & evidence

ORD record
ord-6296394591cb4d9196dd59a65c6dc03f
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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