Reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[NH:12][CH2:13][CH2:14][CH2:15][OH:16].Cl.[O-:18][C:19]#N.[K+]>O>[OH:16][CH2:15][CH2:14][CH2:13][N:12]1[C:3]2[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=2[NH:1][C:19]1=[O:18]Participants
Procedure
To a stirred mixture of 21 parts of 3-{[2-amino-4-(trifluoromethyl)phenyl]amino}-1-propanol and 100 parts of water are added 14.4 parts of hydrochloric acid solution. The whole is stirred for 10 minutes at room temperature. After cooling to 0°-10° C., there is added dropwise a solution of 18 parts of potassium cyanate in 50 parts of water. Upon completion, stirring is continued for 2 hours. The precipitated product is filtered off and dried. Then it is melted and the melt is stirred for 10 minutes. After cooling, it is dissolved in trichloromethane while heating. The solution is filtered and the product is allowed to crystallize from the filtrate. It is filtered off and dried, yielding 8 parts (34%) of 1,3-dihydro-1-(3-hydroxypropyl)-5-(trifluoromethyl)-2H-benzimidazol-2-one.
Workup
- temperatureAfter cooling to 0°-10° C.
- stirringUpon completion, stirring
- waitis continued for 2 hours
- filtrationThe precipitated product is filtered off
- customdried
- stirringthe melt is stirred for 10 minutes
- temperatureAfter cooling
- dissolutionit is dissolved in trichloromethane
- temperaturewhile heating
- filtrationThe solution is filtered
- customto crystallize from the filtrate
- filtrationIt is filtered off
- customdried
Sources & evidence
- ORD record
- ord-c7824292522f4497a8640ecf1cdb2402
- Source dataset
- uspto-grants-1979_11
- Patent number
- US04175129
Linked notes
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