4-Chlorobenzenesulfonyl chloride → HCID 49838021, compound

HRID 1754901Notes

Reaction equation

HRID 1754901 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.Cl.Cl.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[C:29]1[NH:33][C:32](=[O:34])[C:31]2([CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[N:30]=1>ClCCl>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([N:37]2[CH2:36][CH2:35][C:31]3([N:30]=[C:29]([C:23]4[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=4[Cl:21])[NH:33][C:32]3=[O:34])[CH2:39][CH2:38]2)(=[O:17])=[O:16])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 8471TriethylamineHCID 66818214HCID 66818214, compound

Product 1

HCID 49838021HCID 49838021, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (88 μl, 0.632 mmol) and 4-chlorobenzenesulfonyl chloride (70 mg, 0.332 mmol) were added to a mixed solution of 2-(2,4-dichloro-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one dihydrochloride (100 mg, 0.299 mmol) in dichloromethane (3 ml). The reaction solution was stirred at room temperature for 16 hours and then diluted with dichloromethane, and the organic layer was washed with water. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane) to give 8-(4-chloro-benzenesulfonyl)-2-(2,4-dichloro-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one (70.8 mg, 96%).

Workup

  1. washthe organic layer was washed with water
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane)

Sources & evidence

ORD record
ord-bc8110800da84e87a8ed2b861f30072d
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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