2,4-Dichlorobenzoic Acid → HCID 86646333, compound
Reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16]([OH:18])=O.[Cl:24][C:25]1[N:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1.N12CCCN=C1CCCCC2>ClCCl>[Cl:13][C:14]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:15]=1[C:16]([NH:34][S:31]([C:28]1[CH:29]=[N:30][C:25]([Cl:24])=[CH:26][CH:27]=1)(=[O:32])=[O:33])=[O:18]Participants
Procedure
1,1′-Carbonyl-diimidazole (4.22 g, 26 mmol) was added to a solution of 2,4-dichlorobenzoic acid (4.73 g, 24.8 mmol) in 100 ml dichloromethane the mixture was stirred for 30 minutes at room temperature and subsequently refluxed for 30 minutes. Then 6-chloro-pyridine-3-sulfonic acid amide (5.00 g, 26 mmol) and 1,8-diazabicylo[5.4.0]undec-7-en (3.96 g, 26 mmol) were added and the mixture was stirred at room temperature overnight. After evaporation to dryness the residue was taken up with 100 ml ethyl acetate and washed with 1 M HCl and 1 M NaOH and the organic phase was dried over sodium sulphate and concentrated in vacuo. Flash chromatography (SiO2, heptane-ethyl acetate gradient) yielded 6.72 g of the title compound as a white solid, m/z=365 (ES+), 363 (ES−).
Workup
- temperaturesubsequently refluxed for 30 minutes
- stirringthe mixture was stirred at room temperature overnight
- customAfter evaporation to dryness the residue
- washwashed with 1 M HCl and 1 M NaOH
- dry with materialthe organic phase was dried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-00c3683f5e6a4c5b80b783a4da608ba4
- Source dataset
- uspto-grants-2011_02
- Patent number
- US07879884B2
Reaction notes
Loading…