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Sodium Carbonate → 4-(1-Phenylazulene-2-yl)phenylsulfonamide

HRID 1456829
Notes
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Reaction equation

HRID 1456829 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=[CH:9]2)[C:3]=1[C:12](OC)=O.C([NH:20][S:21]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)(=[O:23])=[O:22])(C)(C)C.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:12]1([C:3]2[C:4]3[C:10]([CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[CH:11][C:2]=2[C:27]2[CH:26]=[CH:25][C:24]([S:21]([NH2:20])(=[O:22])=[O:23])=[CH:29][CH:28]=2)[CH:10]=[CH:11][CH:2]=[CH:3][CH:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 221071704-(tert-Butylaminosulphonyl)benzeneboronic acidHCID 22107186Methyl 2-chloroazulene-1-carboxylate

Product 1

HCID 221071814-(1-Phenylazulene-2-yl)phenylsulfonamideYield 277.5%

Reagents, catalysts & solvents 2

HCID 178418397
HCID 178418397, compound
Catalyst
HCID 1140TolueneSolvent

Procedure

Methyl 2-(4-t -butylaminosulfonylphenyl) azulene-1-carboxylate: To a solution of methyl 2-chloroazulene-1-carboxylate (0.50 g) in toluene (20.0 ml) was added 4-t-butylaminosulfonyl-phenylboronic acid (0.87 g), tetrakis(triphenylphosphine)palladium (0) (0.12 g), and 2M aqueous Na2CO3 (4.5 ml), and the reaction mixture was heated under reflux for 16 hr. The mixture was poured into ice-water, followed by extracted with EtOAc. The combined EtOAc extracts were washed with water and brine, dried over Na2SO4, and concentrated. The crude product was purified by SiO2 column chromatography (CHCl3 /EtOAc, 100:1) to give the title compound (1.13 g) as violet crystals; mp 169°-170° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 16 hr
  3. extractionby extracted with EtOAc
  4. washThe combined EtOAc extracts were washed with water and brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude product was purified by SiO2 column chromatography (CHCl3 /EtOAc, 100:1)

Sources & evidence

ORD record
ord-10edb3f5982a4d2db21a0676d24832d7
Source dataset
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05843999

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes