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Sodium Hydroxide → 5-(Dimethylamino)methyl-2-mercaptomethyl-4-methylthiophene

HRID 892788
Notes
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Reaction equation

HRID 892788 reaction equation
Cl.Cl.C([S:6][CH2:7][C:8]1[S:9][C:10]([CH2:14][N:15]([CH3:17])[CH3:16])=[C:11]([CH3:13])[CH:12]=1)(=N)N.[OH-].[Na+]>O>[CH3:17][N:15]([CH2:14][C:10]1[S:9][C:8]([CH2:7][SH:6])=[CH:12][C:11]=1[CH3:13])[CH3:16]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 138252712-Amidinothiomethyl-5-(dimethylamino)methyl-4-methylthiophene dihydrochloride

Product 1

HCID 138252725-(Dimethylamino)methyl-2-mercaptomethyl-4-methylthiopheneYield 83.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 5 ml of water was dissolved 10 g of 2-amidinothiomethyl-5-(dimethylamino)methyl-4-methylthiophene dihydrochloride, and 2.52 g of sodium hydroxide was added thereto, and the resulting mixture was subjected to reaction under reflux for 2.5 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and then extracted with 100 ml of methylene chloride, and the extract was dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The oily substance thus obtained was distilled under reduced pressure in a nitrogen atmosphere to obtain 5.3 g (yield 83%) of 5-(dimethylamino)methyl-2-mercaptomethyl-4-methylthiophene having a boiling point of 102°-105° C./3 mmHg.

Workup

  1. additionwas added
  2. customthe resulting mixture was subjected to reaction
  3. temperatureunder reflux for 2.5 hours in a nitrogen atmosphere
  4. extractionextracted with 100 ml of methylene chloride
  5. dry with materialthe extract was dried over anhydrous magnesium sulfate
  6. customafter which the solvent was removed by distillation under reduced pressure
  7. customThe oily substance thus obtained
  8. distillationwas distilled under reduced pressure in a nitrogen atmosphere

Sources & evidence

ORD record
ord-9f35b51cd98a4f30acf7b555f04a38b0
Source dataset
uspto-grants-1992_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05120746

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes