5-Bromo-2-methoxybenzene-1-sulfonyl chloride → HCID 9850299, compound

HRID 2116534Notes

Reaction equation

HRID 2116534 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:15]=[C:16]([Cl:20])[CH:17]=[N:18][CH:19]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Br:21][C:22]1[CH:23]=[CH:24][C:25]([O:32][CH3:33])=[C:26]([S:28](Cl)(=[O:30])=[O:29])[CH:27]=1>ClCCl>[CH3:33][O:32][C:25]1[CH:24]=[CH:23][C:22]([Br:21])=[CH:27][C:26]=1[S:28]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:13][C:14]2[CH:15]=[C:16]([Cl:20])[CH:17]=[N:18][CH:19]=2)=[C:6]([CH:12]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:30])=[O:29]

Participants

4

Reactant 2

HCID 5200205-Bromo-2-methoxybenzene-1-sulfonyl chlorideHCID 9948021HCID 9948021, compound

Product 1

HCID 9850299HCID 9850299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Alternatively, poly(4-vinylpyridine) (250 mg, 60 mesh) can be washed with dichloromethane (2×7 mL) and diluted into dichloromethane (2 mL). The aniline produced in Example 1 (29.2 mg, 0.1 mmol) can be added followed by 5-bromo-2-methoxybenzenesulfonyl chloride (59 mg, 0.25 mmol). The reaction vessel is then agitated for ten hours and ArgoPore-NH2 (0.50 g, 1.11 mmol/gram loading) is added along with dichloromethane (6 mL). The reaction vessel is agitated for three hours and the solvent is collected. The resin is washed with dichloromethane (2×6 mL) and the dichloromethane is combined and evaporated to yield the title compound.

Workup

  1. washAlternatively, poly(4-vinylpyridine) (250 mg, 60 mesh) can be washed with dichloromethane (2×7 mL)
  2. additiondiluted into dichloromethane (2 mL)
  3. stirringThe reaction vessel is agitated for three hours
  4. customthe solvent is collected
  5. washThe resin is washed with dichloromethane (2×6 mL)
  6. customevaporated

Sources & evidence

ORD record
ord-1e79f3a922d8424da2dc7375e609ee32
Source dataset
uspto-grants-2008_10
Patent number
US07439242B2

Reaction notes

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