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4-Toluenesulfonyl chloride → 2,2,4,6,7-Pentamethyl-5-(p-toluenesulfonylamino)-2,3-dihydrobenzofuran

HRID 1493049
Notes
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Reaction equation

HRID 1493049 reaction equation
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]2[O:9][C:8]([CH3:11])([CH3:10])[CH2:7][C:6]=2[C:12]=1[CH3:13].[C:16]1([CH3:26])[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1.ClCCl.C(OC(C)C)(C)C>N1C=CC=CC=1>[CH3:11][C:8]1([CH3:10])[CH2:7][C:6]2[C:12]([CH3:13])=[C:2]([NH:1][S:22]([C:19]3[CH:20]=[CH:21][C:16]([CH3:26])=[CH:17][CH:18]=3)(=[O:24])=[O:23])[C:3]([CH3:15])=[C:4]([CH3:14])[C:5]=2[O:9]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 100358625-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuranHCID 22238436Dichloromethane diisopropylether

Product 1

HCID 106422232,2,4,6,7-Pentamethyl-5-(p-toluenesulfonylamino)-2,3-dihydrobenzofuranYield 68.8%

Reagents, catalysts & solvents 1

HCID 1049Pyridine
Solvent

Conditions

Temperature
50 °C

Procedure

5-Amino-2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran (2.00 g, 9.74 mmol) and p-toluenesulfonyl chloride (2.04 g, 10.7 mmol) were dissolved in pyridine (30 ml) and stirred at 50° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in chloroform. The mixture was washed with 1N hydrochloric acid and saturated saline and dried and then the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (hexane-ethyl acetate, 97:3). The crude crystals were recrystallized from dichloromethane-isopropyl ether to obtain the desired compound (2.41 g, yield: 68.8% yield), m.p. 219°-220° C. (dichloromethane-isopropyl ether).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in chloroform
  3. washThe mixture was washed with 1N hydrochloric acid and saturated saline
  4. customdried
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (hexane-ethyl acetate, 97:3)
  7. customThe crude crystals were recrystallized from dichloromethane-isopropyl ether

Sources & evidence

ORD record
ord-fe23a556e6a14d6ba37581c9a879a838
Source dataset
uspto-grants-1994_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05376681

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes