Hydrochloric Acid → HCID 54556725, compound
Reaction equation
[CH:1](N(C(C)C)CC)(C)C.[Cl-].[C:11]([O:22][CH3:23])(=[O:21])[C:12]1[CH:20]=[CH:19][C:15](C([O-])=O)=[CH:14][CH:13]=1.C1C(C(N)=N)=CC=C(OCCCCCO[C:40]2[CH:45]=[CH:44][C:43](/[C:46](/[NH2:49])=[N:47]\[OH:48])=CC=2)C=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>C1COCC1.C(Cl)Cl.O>[CH2:43]([C:46]1[N:49]=[C:1]([C:20]2[CH:19]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]([O:22][CH3:23])=[O:21])[O:48][N:47]=1)[CH2:44][CH2:45][CH3:40]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Procedure
Diisopropylethylamine (1.1 ml, 6.0 mmol) was added to a solution of terephthalic acid, monomethyl ester chloride (1.0 g, 5.0 mmol) and N-hydroxypentamidine (0.70 g, 6.0 mmol) in THF (8 mL). After stirring at ambient temperature for 1 hour, cesium carbonate (3.6 g, 11 mmol) was added and the reaction was stirred at 50° C. After stirring at 50° C. for 3.5 hours, the reaction was transferred to a separatory funnel with CH2Cl2/H2O. The aqueous layer was acidified with 1N HCl to pH 1 and extracted with CH2Cl2 (3×40 mL). The combined organic layers were dried (MgSO4) and concentrated in vacuo. Flash chromatography (silica, 50 mm dia, 10% EtOAc/hexane) afforded 1.2 g (93%) of methyl (3-butyl-1,2,4-oxadiazol-5-yl)benzoate.
Workup
- stirringthe reaction was stirred at 50° C
- stirringAfter stirring at 50° C. for 3.5 hours
- extractionextracted with CH2Cl2 (3×40 mL)
- dry with materialThe combined organic layers were dried (MgSO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9b1409d8ba994d1b8bd54e385b21a54a
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06624309B1
Reaction notes
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