Ethanol → 2-Imino-5-[4-[2-(5-methyl-2-phenyl-oxazole-4-yl)-ethoxy]-benzothiophene-7-yl]-methyl-thiazolidine-4-one
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:21]2[CH:22]=[CH:23][S:24][C:20]=2[C:19](N)=[CH:18][CH:17]=1.[NH2:26][C:27]([NH2:29])=[S:28].[C:30]([O-:33])(=O)[CH3:31].[Na+].[CH2:35](O)C>>[NH:26]=[C:27]1[N:29]([CH3:35])[C:30](=[O:33])[CH:31]([C:19]2[C:20]3[S:24][CH:23]=[CH:22][C:21]=3[C:16]([O:15][CH2:14][CH2:13][C:3]3[N:4]=[C:5]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[O:6][C:2]=3[CH3:1])=[CH:17][CH:18]=2)[S:28]1Participants
5
Conditions
- Temperature
- 2 °C
Procedure
190 g (0.380 mol) of 5-methyl-4-[2-(7-amino-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole were suspended in 2.85 l of ethanol. 31.6 g (0.415 mol) of thiourea and 34.8 g of sodium acetate were added. After boiling for about 18 hours (reflux) the reaction mixture was cooled to 0 to 4° C. and stirred for 1.5 hours at this temperature. The precipitate was filtered with suction and washed twice with 250 ml cold ethanol. 1.9 l of water was added to the residue, the mixture was stirred for 10 minutes and the precipitate was filtered with suction and dried for 24 hours at 80° C. (vacuum).
Workup
- temperature(reflux) the reaction mixture
- filtrationThe precipitate was filtered with suction
- washwashed twice with 250 ml cold ethanol
- addition1.9 l of water was added to the residue
- stirringthe mixture was stirred for 10 minutes
- filtrationthe precipitate was filtered with suction
- customdried for 24 hours at 80° C. (vacuum)
Sources & evidence
- ORD record
- ord-2c96f660d2b14ad39d0ddd490f22bcc8
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06482958B2
Reaction notes
Loading…