Benzenesulfonyl chloride → HCID 8189263, compound

HRID 1725869Notes

Reaction equation

HRID 1725869 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1>[Br:12][C:9]1[CH:10]=[CH:11][C:2]([NH:1][S:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:21])=[O:20])=[C:3]([CH:8]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 736224Methyl 2-amino-5-bromobenzoate

Product 1

HCID 8189263HCID 8189263, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of methyl 2-amino-5-bromobenzoate (23.34 g, 101 mmol) in pyridine (100 mL) was treated with a solution of benzenesulfonyl chloride (14 mL, 110 mmol), stirred for 16 hours at ambient temperature, and concentrated. The concentrate was dissolved in dichloromethane, washed twice with 1N NaHSO4, dried (MgSO4), filtered, and concentrated. The concentrate was recrystallized from 3:1 ethanol/water (200 mL) to provide the desired product (33.4 g). MS (DCI) m/e 387, 389 (M+NH4)+; 1H NMR (300 MHz, DMSO-d6) δ 10.32 (s, 1H), 7.91 (d, 1H), 7.80 (d, 1H), 7.77 (s, 1H), 7.75 (dd, 1H), 7.66 (d, 1H), 7.61-7.53 (m, 2H), 7.39 (d, 1H), 3.79 (s, 3H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in dichloromethane
  3. washwashed twice with 1N NaHSO4
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was recrystallized from 3:1 ethanol/water (200 mL)

Sources & evidence

ORD record
ord-a0bde89796c141769b6f55010513b420
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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