5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 10801728, compound

HRID 745851Notes

Reaction equation

HRID 745851 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.[C:15]([N:17]=[CH:18][O-])#[N:16]>C(#N)C>[C:15]([NH:17][CH:18]=[N: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)#[N:16]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 178512387HCID 178512387, compound

Product 1

HCID 10801728HCID 10801728, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5.6 g of 5-[[(2-aminoethyl)thio]methyl]N,N-dimethylfuranmethanamine (prepared according to Belgian Pat. No. 857,388, hereby incorporated by reference) in 35 ml of acetonitrile are added dropwise 2.56 g of N-cyano-formimidate in 15 ml of acetonitrile, under cooling at 0° C. The mixture is maintained under stirring for 30 minutes and the acetonitrile is removed by vacuum evaporation. A solid residue is formed, which is crystallized from ethyl acetate. 2.1 g are obtained of N-cyano-N'-[2-[[[5-[(dimethyl-amino)methyl]-2-furanyl]methyl]thio]ethyl]formamidine.

Workup

  1. temperatureThe mixture is maintained
  2. customthe acetonitrile is removed by vacuum evaporation
  3. customA solid residue is formed
  4. customwhich is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-a296dfb8caaa4e0691dd2df5b3a12b5c
Source dataset
uspto-grants-1986_07
Patent number
US04600780

Reaction notes

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