Triethylamine → HCID 54019574, compound

HRID 342466Notes

Reaction equation

HRID 342466 reaction equation
[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[C:15]2[O:14][C:13]3[CH2:16][CH2:17][CH2:18][CH:19](O)[C:12]=3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5].CS(Cl)(=O)=O.C(N(CC)CC)C>ClCCl>[Cl:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:3]=1[C:4]([NH:6][C:7]1[C:15]2[O:14][C:13]3[CH2:16][CH2:17][CH:18]=[CH:19][C:12]=3[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[O:5]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 54535018HCID 54535018, compound

Product 1

HCID 54019574HCID 54019574, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-(2,6-dichlorobenzoylamino)-1-hydroxy-1,2,3,4-tetrahydrodibenzofuran (500 mg), methanesulfonyl chloride (880 mg) and triethylamine (1.19 g) in dichloromethane was refluxed for 4 hours. The mixture was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from a mixture of 2-propanol and water to give 6-(2,6-dichlorobenzoylamino)-3,4-dihydrodibenzofuran (173 mg).

Workup

  1. temperaturewas refluxed for 4 hours
  2. washThe mixture was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel
  6. customthe obtained oil was crystallized from a mixture of 2-propanol and water

Sources & evidence

ORD record
ord-8a795a4c79bd4839aa711ca8774838bd
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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