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Ethanol → 2-Imino-5-[4-[2-(5-methyl-2-phenyl-oxazole-4-yl)-ethoxy]-benzothiophene-7-yl]-methyl-thiazolidine-4-one

HRID 1596798
Notes
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Reaction equation

HRID 1596798 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]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 702EthanolHCID 517045Sodium AcetateHCID 2723790ThioureaHCID 154856655-Methyl-4-[2-(7-amino-benzothiophene-4-yloxy)-ethyl]-2-phenyl-oxazole

Product 1

HCID 184022522-Imino-5-[4-[2-(5-methyl-2-phenyl-oxazole-4-yl)-ethoxy]-benzothiophene-7-yl]-methyl-thiazolidine-4-one

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

  1. temperature(reflux) the reaction mixture
  2. filtrationThe precipitate was filtered with suction
  3. washwashed twice with 250 mnl cold ethanol
  4. addition1.91 of water was added to the residue
  5. stirringthe mixture was stirred for 10 minutes
  6. filtrationthe precipitate was filtered with suction
  7. customdried for 24 hours at 80° C. (vacuum)

Sources & evidence

ORD record
ord-4338e03645c048cc864b9c1b7be042f3
Source dataset
uspto-grants-2001_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06291685B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes