Thiophenol → HCID 59300778, compound

HRID 2235479Notes

Reaction equation

HRID 2235479 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[CH2:11][C:12]1[NH:31][C:15]2=[CH:16][C:17]3[C:18]([CH3:30])([CH3:29])[C:19](=[O:28])[N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:21]=3[CH:22]=[C:14]2[N:13]=1.ClC1C=C(C(OO)=[O:40])C=CC=1>C(Cl)Cl>[C:1]1([S:7]([CH2:11][C:12]2[NH:31][C:15]3=[CH:16][C:17]4[C:18]([CH3:30])([CH3:29])[C:19](=[O:28])[N:20]([CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[C:21]=4[CH:22]=[C:14]3[N:13]=2)=[O:40])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 7969ThiophenolHCID 24758Sodium hydrideHCID 70297m-Chloroperbenzoic acidHCID 67426354HCID 67426354, compound

Product 1

HCID 59300778HCID 59300778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of thiophenol (70 μl) in CH2Cl2 (4 ml) is added NaH (43 mg; 1.08 mmol) and the resulting suspension is stirred for 5 min at RT. Then freshly prepared 2-chloromethyl-7,7-dimethyl-5-pentyl-5,7-dihydro-1H-imidazo[4,5-f]indol-6-one (265 mg) dissolved in CH2Cl2 (5 ml) is added and the mixture is stirred at 40° C. for 20 h. After cooling to 0° C. 3-chloro-benzenecarboperoxoic acid (186 mg; 0.83 mmol) is added and stirring is continued for another 3 h. After completion of the reaction the mixture is concentrated in vacuo and purified by NP-HPLC eluting with CH2Cl2/MeOH to give the desired compound (5.8 mg).

Workup

  1. additionis added
  2. stirringthe mixture is stirred at 40° C. for 20 h
  3. temperatureAfter cooling to 0° C
  4. stirringstirring
  5. waitis continued for another 3 h
  6. customAfter completion of the reaction the mixture
  7. concentrationis concentrated in vacuo
  8. custompurified by NP-HPLC
  9. washeluting with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-a8e17caf8e2a4f889db52749e12eaaee
Source dataset
uspto-grants-2010_05
Patent number
US07714010B2

Reaction notes

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