Hydrochloric Acid → HCID 20081446, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][S:12]([CH:15]([CH:20]([CH3:22])[CH3:21])[C:16](OC)=[O:17])(=[O:14])=[O:13])[N:4]=1.C([NH2:25])=O.C[O-].[Na+].Cl>CN(C)C=O.O.CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][S:12]([CH:15]([CH:20]([CH3:22])[CH3:21])[C:16]([NH2:25])=[O:17])(=[O:14])=[O:13])[N:4]=1Participants
8
Conditions
- Temperature
- 100 °C
Procedure
A solution of the product of Example 1 (3.0 g) and formamide (1.22 g) in dimethylformamide (10 ml) was heated to 80° C. Sodium methoxide (3.3 ml of a 25% w/v methanol solution) was slowly introduced with stirring. The reaction mixture was maintained at about 100° C. for 4 hours prior to addition to water (150 ml) and acidification (hydrochloric acid). The product was extracted into ethyl acetate, the ethyl acetate solution being washed with water (twice), dried over magnesium sulfate and run down under vacuum. The residual oil was triturated with a mixture of diethyl and diisopropyl ethers to yield a white solid. The solid was washed thoroughly with the ether mixture and dried. The yield was 1.1 g (39%), mp 147°-50° C.
Workup
- extractionThe product was extracted into ethyl acetate
- washthe ethyl acetate solution being washed with water (twice),
- dry with materialdried over magnesium sulfate
- customThe residual oil was triturated with a mixture of diethyl and diisopropyl ethers
- customto yield a white solid
- washThe solid was washed thoroughly with the ether mixture
- customdried
Sources & evidence
- ORD record
- ord-950805c4f25d4cd289b2b9296debdbc4
- Source dataset
- uspto-grants-1995_03
- Patent number
- US05401710
Reaction notes
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