Benzenesulfonyl chloride → HCID 22394691, compound

HRID 1071787Notes

Reaction equation

HRID 1071787 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH2:9][CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1.[H-].[Na+].[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10]1[CH:9]([S:24]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:26])=[O:25])[CH2:8][CH2:7][C:6](=[O:15])[C:5]2=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 3357036-Chloro-4-oxo-1,2,3,4-tetrahydrocarbazole

Product 1

HCID 22394691HCID 22394691, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6-chloro-4-oxo-1,2,3,4-tetrahydrocarbazole (109 mg, 0.5 mmol) in THF is treated with NaH (60 mg, 60% dispersion in mineral oil, 1.5 mmol), stirred for 30 min., treated with phenylsulfonyl chloride (132 mg, 0.5 mmol), shaken for 8 h and concentrated in vacuo. The resultant residue is dissolved in ethyl acetate, washed with water and reconcentrated in vacuo to afford the title product which is used as is in Example 134.

Workup

  1. stirringshaken for 8 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resultant residue is dissolved in ethyl acetate
  4. washwashed with water

Sources & evidence

ORD record
ord-4f3f06609c2c45baa53a97af48a1591f
Source dataset
uspto-grants-2005_06
Patent number
US06906095B2

Reaction notes

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