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4-Methoxybenzenesulfonyl chloride → N-[2-[(4-Hydroxyphenyl)amino]-3-pyridinyl]-4-methoxybenzenesulfonamide

HRID 270666
Notes
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Reaction equation

HRID 270666 reaction equation
[NH2:1][C:2]1[C:3]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24](Cl)(=[O:26])=[O:25])=[CH:20][CH:19]=1>N1C=CC=CC=1.C1COCC1>[OH:15][C:12]1[CH:13]=[CH:14][C:9]([NH:8][C:3]2[C:2]([NH:1][S:24]([C:21]3[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:23][CH:22]=3)(=[O:26])=[O:25])=[CH:7][CH:6]=[CH:5][N:4]=2)=[CH:10][CH:11]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 108565254-[(3-aminopyridin-2-yl)amino]phenol

Product 1

HCID 3035714N-[2-[(4-Hydroxyphenyl)amino]-3-pyridinyl]-4-methoxybenzenesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of EXAMPLE 2 in pyridine (9 mL/g) at 0° C. was treated with a mixture of para-methoxybenzenesulfonyl chloride (1.05 equivalents) in THF (1.4 mL/g) at 0° C. at a rate which kept the reaction temperature below 5° C., warmed to 25° C., stirred for 15 minutes, and concentrated. The concentrate was treated with n-propanol to provide a composition having 9% pyridine in the solvent mixture and to precipitate a solid. The mixture was cooled to 0° C. and filtered. The filtrant and washed with ethyl acetate (5-7 mL/g starting material) and dried at 45° C.

Workup

  1. customthe reaction temperature below 5° C.
  2. concentrationconcentrated
  3. additionThe concentrate was treated with n-propanol
  4. customto provide a composition
  5. customto precipitate a solid
  6. temperatureThe mixture was cooled to 0° C.
  7. filtrationfiltered
  8. washThe filtrant and washed with ethyl acetate (5-7 mL/g starting material)
  9. customdried at 45° C.

Sources & evidence

ORD record
ord-8dbac5cc4b304faf922904c85cb42547
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07449584B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes