Water → HCID 12913952, compound

HRID 224861Notes

Reaction equation

HRID 224861 reaction equation
[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1[S:7][C:8]([CH2:11]O)=[CH:9][CH:10]=1)[CH3:4].Cl.[NH2:14][CH2:15][CH2:16][SH:17].O.[OH-].[Na+]>Cl.CCOCC.C(O)C>[ClH:1].[ClH:1].[CH3:2][N:3]([CH2:5][C:6]1[S:7][C:8]([CH2:11][S:17][CH2:16][CH2:15][NH2:14])=[CH:9][CH:10]=1)[CH3:4]

Participants

8

Reactant 4

HCID 962WaterHCID 9082Cysteamine HydrochlorideHCID 14798Sodium HydroxideHCID 12788073HCID 12788073, compound

Product 1

HCID 12913952HCID 12913952, compoundYield 144.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent3×HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 2-(dimethylaminomethyl)-5-(hydroxymethyl)thiophene hydrochloride (8.0 g) in concentrated hydrochloric acid (50 ml) was added dropwise to a stirred solution of cysteamine hydrochloride (4.37 g) in concentrated hydrochloric acid (50 ml) cooled in an ice-bath. The temperature of the mixture was maintained below 5° during the addition. The mixture was allowed to reach room temperature and was stirred overnight and poured into water. The aqueous mixture was adjusted to pH 12 with 2 N sodium hydroxide and was extracted with ethyl acetate (750 ml). The extract was dried and evaporated to give an oil which was dissolved in dry ether and hydrogen chloride in ethanol was added and the solid was filtered off to give 2-[5-dimethylaminomethyl-2-thienylmethylthio]ethylamine dihydrochloride (8.44 g) m.p. 190°-194°.

Workup

  1. temperaturecooled in an ice-bath
  2. temperatureThe temperature of the mixture was maintained below 5° during the addition
  3. customto reach room temperature
  4. extractionwas extracted with ethyl acetate (750 ml)
  5. customThe extract was dried
  6. customevaporated
  7. customto give an oil which
  8. filtrationthe solid was filtered off

Sources & evidence

ORD record
ord-b9f5930a08cc4dd2acb6144ebc00fc92
Source dataset
uspto-grants-1980_11
Patent number
US04234588

Reaction notes

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