Sodium hydride → HCID 71270517, compound

HRID 2281178Notes

Reaction equation

HRID 2281178 reaction equation
[H-].[Na+].[C:3]1([C:9]2[O:10][CH:11]=[C:12]3[C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[NH:14][C:13]=23)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1OCCOCCOCCOCCOC1.[Br:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43](Cl)(=[O:45])=[O:44]>C1COCC1>[Br:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43]([N:14]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:12]2=[CH:11][O:10][C:9]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[C:13]12)(=[O:45])=[O:44]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 5204032-Bromobenzenesulfonyl chlorideHCID 67464347HCID 67464347, compound

Product 1

HCID 71270517HCID 71270517, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

2.1 g (52.5 mmol) of NaH (60% in mineral oil) are dissolved in 500 ml of THF under a protective-gas atmosphere. 11.5 g (50 mmol) of 3-phenyl-4H-furo[3,4-b]indole and 11.5 g (52.5 mmol) of 15-crown-5 dissolved in 200 ml of THF are added. After 1 h at room temperature, a solution of 12.7 g (55 mmol) of 2-bromobenzenesulfonyl chloride in 250 ml of THF is added dropwise. The reaction mixture is stirred at room temperature for 18 h. After this time, the reaction mixture is poured onto ice and extracted three times with dichloromethane. The combined organic phases are dried over Na2SO4 and evaporated. The residue is extracted with hot toluene and recrystallised from toluene/n-heptane. The yield is 16 g (75%).

Workup

  1. additionare added
  2. additionAfter this time, the reaction mixture is poured onto ice
  3. extractionextracted three times with dichloromethane
  4. dry with materialThe combined organic phases are dried over Na2SO4
  5. customevaporated
  6. extractionThe residue is extracted with hot toluene
  7. customrecrystallised from toluene/n-heptane

Sources & evidence

ORD record
ord-d4cde928e0f240529216468ee45aac95
Source dataset
uspto-grants-2015_09
Patent number
US09139582B2

Reaction notes

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