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 1 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 mnl cold ethanol. 1.91 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 mnl cold ethanol
- addition1.91 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-4338e03645c048cc864b9c1b7be042f3
- Source dataset
- uspto-grants-2001_09
- Patent number
- US06291685B1
Reaction notes
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