5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 178504070, compound

HRID 1277999Notes

Reaction equation

HRID 1277999 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:10][C:9]([CH2:11][N:12]([CH3:14])[CH3:13])=[CH:8][CH:7]=1.[CH3:15][S:16]([N:19]=[C:20](SC)[S:21][CH3:22])(=[O:18])=[O:17]>C(OCC)(=O)C>[CH3:13][N:12]([CH2:11][C:9]1[O:10][C:6]([CH2:5][S:4][CH2:3][CH2:2][NH:1][C:20]([S:21][CH3:22])=[N:19][S:16]([CH3:15])(=[O:18])=[O:17])=[CH:7][CH:8]=1)[CH3:14]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 13449843N-[bis(methylsulfanyl)methylidene]methanesulfonamide

Product 1

HCID 178504070HCID 178504070, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-[[(2-aminoethyl)thio]methyl]-N,N-dimethyl-furanmethanamine (2.97 g) and methylsulphonylcarbonimidodithioic acid, dimethyl ester (4.0 g) in ethyl acetate (250 ml) was refluxed for 18 hours. The mixture was washed with acetic acid (0.126 ml) in water (20 ml) three times, the aqueous extracts combined and the pH adjusted to 9 with 8% aqueous potassium carbonate. The oily suspension was extracted with ethyl acetate (3×125 ml), the combined extracts dried (magnesium sulphate) and evaporated to dryness to give the title compound (4 g) as a yellow oil.

Workup

  1. temperaturewas refluxed for 18 hours
  2. washThe mixture was washed with acetic acid (0.126 ml) in water (20 ml) three times
  3. extractionThe oily suspension was extracted with ethyl acetate (3×125 ml)
  4. dry with materialthe combined extracts dried (magnesium sulphate)
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-82202389d44b45cbbfd80cadcd845969
Source dataset
uspto-grants-1981_07
Patent number
US04279911

Reaction notes

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