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Methanol → (E,E)-3-Carboxymethyl-5-(2-methylcinnamylidene)rhodanine N-methyl-D-glucamine salt

HRID 414248
Notes
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Reaction equation

HRID 414248 reaction equation
[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].[C:14]([CH2:17][N:18]1[C:22](=[O:23])[C:21](=[CH:24][CH:25]=[CH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])[S:20][C:19]1=[S:34])([OH:16])=[O:15].S1CC(=O)NC1=S.CO>O>[CH3:1][NH:2][CH2:3][C@@H:4]([C@H:6]([C@@H:8]([C@@H:10]([CH2:12][OH:13])[OH:11])[OH:9])[OH:7])[OH:5].[C:14]([CH2:17][N:18]1[C:22](=[O:23])/[C:21](=[CH:24]\[CH:25]=[CH:26]\[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[CH3:33])/[S:20][C:19]1=[S:34])([OH:16])=[O:15]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 887MethanolHCID 8567N-Methyl-D-glucamineHCID 1201546RhodanineHCID 566395213-Carboxymethyl-5-(2-methylcinnamylidene)rhodanine

Product 1

HCID 86739588(E,E)-3-Carboxymethyl-5-(2-methylcinnamylidene)rhodanine N-methyl-D-glucamine saltYield 72.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.001 g of N-methyl-D-glucamine in 20 ml of water was added 3.194 g of 3-carboxymethyl-5-(2-methylcinnamylidene)rhodanine [prepared as described in Example 1 (35)], and the mixture was heated to dissolve the rhodanine derivative, and then 40 ml of methanol was added to the solution at the same temperature. The mixture was cooled to room temperature and the precipitated crystals were filtered. The resulting crystals were washed with 5 ml of mixture of water and methanol (1:2), and 5 ml of methanol, and dried under reduced pressure to obtain 3.73 g of the titled compound.

Workup

  1. temperaturethe mixture was heated
  2. filtrationthe precipitated crystals were filtered
  3. washThe resulting crystals were washed with 5 ml of mixture of water and methanol (1:2), and 5 ml of methanol
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-bc79d3d1938e452ca088cff574954242
Source dataset
uspto-grants-1988_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04791126

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes