Hydrochloric Acid → N-(2-phenylbenzo[b]thiophen-3-ylsulfonyl)-N'-(4-methoxy-6-methylprimidin-2-yl)urea
Reaction equation
[C:1]1([C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[S:16]([NH-:19])(=[O:18])=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:20][O:21][C:22]1[CH:27]=[C:26]([CH3:28])[N:25]=[C:24]([N:29](C2C=CC=CC=2)[C:30](=O)[O-:31])[N:23]=1.N12CCCN=C1CCCCC2.Cl>O.O1CCOCC1>[C:1]1([C:7]2[S:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[C:8]=2[S:16]([NH:19][C:30]([NH:29][C:24]2[N:23]=[C:22]([O:21][CH3:20])[CH:27]=[C:26]([CH3:28])[N:25]=2)=[O:31])(=[O:18])=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 1.1 g (3.8 mmol) of 2-phenylbenzo[b]thiophen-3-ylsulfonylamide, 1.0 g (3.8 mmol) of N-(4-methoxy-6-methylpyrimidin-2-yl)phenylcarbamate, 0.6 g (4 mmol) of 1.8-diazabicyclo[5.4.0]undec-7-ene and 15 ml of dioxane is stirred for 4 hours at 20°-25° C. The reaction mixture is then taken up in 100 ml of water, acidified to pH 3 by adding 2N hydrochloric acid dropwise and then extracted with 3×30 ml of ethyl acetate. The combined extracts are dried and concentrated by evaporation. The residue is crystallised from ether, affording 1.35 g (78% of theory) of N-(2-phenylbenzo[b]thiophen-3-ylsulfonyl)-N'-(4-methoxy-6-methylprimidin-2-yl)urea with a melting point of 199°-202° C.
Workup
- extractionextracted with 3×30 ml of ethyl acetate
- customThe combined extracts are dried
- concentrationconcentrated by evaporation
- customThe residue is crystallised from ether
Sources & evidence
- ORD record
- ord-15176f966b484ffdb2bbc2914de7398b
- Source dataset
- uspto-grants-1990_06
- Patent number
- US04932997
Reaction notes
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