Methanesulfonic Acid → N-(2,3-dihydro-benzo[b]furan-7-sulfonyl)-N'-(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-urea
Reaction equation
[S:1]([C:5]1[C:10]2[O:11][CH2:12][CH2:13][C:9]=2[CH:8]=[CH:7][CH:6]=1)(=[O:4])(=[O:3])[NH2:2].[C:14](=[O:29])(OC1C=CC=CC=1)OC1C=CC=CC=1.[N:30]12CCC[N:37]=[C:36]1CCCCC2.C1C[CH2:50][N:49]2[C:44](=[N:45][CH2:46]C[CH2:48]2)CC1.CS(O)(=O)=O.NN1N=C(N(C)C)C=[C:60]([O:67]C)[NH:59]1>C(#N)C>[O:11]1[CH2:12][CH2:13][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([S:1]([NH:2][C:60]([NH:59][C:46]3[N:45]=[C:44]([N:49]([CH3:48])[CH3:50])[N:30]=[C:36]([O:29][CH3:14])[N:37]=3)=[O:67])(=[O:4])=[O:3])[C:10]1=2Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
8,0 g of 2,3-dihydro-7-sulfamoyl-benzo[b]furan (0,04 mol) and 7,1 g of diphenyl carbonate (0,04 mol) and 150 ml of acetonitrile are stirred together. To this suspension are added dropwise at 0°-5° C. 7,1 g (0,05 mol) of 1,8-diazabicyclo(5,4,0)-undec-7-ene DBU and the resulting solution is left to stand for 15 hours at room temperature. These are then added dropwise 4,4 g (0,045 mol) of methanesulfonic acid at 0°-5° C. An addition of 6,8 g (0,04 mol) of 2-amino-4-dimethylamino-6-methoxy-triazine is subsequently made and the resulting suspension is refluxed for two hours and the resulting turbid hot solution is filtered.
Workup
- additionTo this suspension are added dropwise at 0°-5° C
- temperaturethe resulting suspension is refluxed for two hours
- filtrationthe resulting turbid hot solution is filtered
Sources & evidence
- ORD record
- ord-6ec1709cce1b42df98d4de645bc9352d
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04656273
Reaction notes
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