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

HRID 1456831
Notes
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Reaction equation

HRID 1456831 reaction equation
C([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:23]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=[CH:22]3)[C:16]=2C(OC)=O)=[CH:11][CH:10]=1)(=[O:8])=[O:7])(C)(C)C.C1(B(O)O)C=CC=CC=1.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:25]1([C:24]2[C:23]3[C:17]([CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:16][C:15]=2[C:12]2[CH:13]=[CH:14][C:9]([S:6]([NH2:5])(=[O:7])=[O:8])=[CH:10][CH:11]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 11145169HCID 11145169, compound

Product 1

HCID 221071814-(1-Phenylazulene-2-yl)phenylsulfonamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 1140
Toluene
Solvent

Procedure

Methyl 2- (4-t-butylaminosulfonylphenyl) -3-phenylazulene-1-carboxylate: To a solution of methyl 3-bromo-2-(4-t-butylaminosulfonylphenyl) azulene-1-carboxlate (0.56 g) in toluene (10.0 ml) was added phenylboronic acid (0.34 g), tetrakis(triphenylphosphine)palladium (0) (0.07 g) and 2M aqueous Na2CO3 (2.3 ml), and the reaction mixture was heated under reflux for 2 hr. The reaction 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 (benzenee/EtOAc, 20:1) to give the title compound (0.47 g) as violet crystals; mp 76°-77° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 2 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 (benzenee/EtOAc, 20:1)

Sources & evidence

ORD record
ord-253ed14ad9e94e1ca4ec4e3ce1406fe8
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