5-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamine → HCID 178483223, compound

HRID 1154724Notes

Reaction equation

HRID 1154724 reaction equation
CS[C:3]1[C:7]2=[CH:8][S:9][CH:10]=[C:6]2[S:5](=[O:12])(=[O:11])[N:4]=1.[CH3:13][N:14]([CH2:16][C:17]1[O:21][C:20]([CH2:22][S:23][CH2:24][CH2:25][NH2:26])=[CH:19][CH:18]=1)[CH3:15]>C(O)C>[CH3:15][N:14]([CH2:16][C:17]1[O:21][C:20]([CH2:22][S:23][CH2:24][CH2:25][NH:26][C:3]2[C:7]3=[CH:8][S:9][CH:10]=[C:6]3[S:5](=[O:11])(=[O:12])[N:4]=2)=[CH:19][CH:18]=1)[CH3:13]

Participants

4

Reactant 2

HCID 1622035-(((2-Aminoethyl)thio)methyl)-N,N-dimethyl-2-furanmethanamineHCID 13390866HCID 13390866, compound

Product 1

HCID 178483223HCID 178483223, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 1.8 g. (0.0082 m.) of 3-(methylthio)thieno[3,4-d]isothiazole-1,1-dioxide in 10 ml. of ethanol is added 1.76 g. (0.0082 m.) of 2-[[[5-[(dimethylamino)methyl]-2-furanyl]methyl]thio]ethylamine with stirring at room temperature. The reaction mixture is heated to reflux and heating is continued for 1.5 hours. At this time the reaction mixture is filtered to remove insoluble material and then evaporated to dryness. The product is purified using a silica gel column with methanol as the eluant. The desired fraction was evaporated to dryness and then triturated with ether to give 120 mg. a white solid with a m.p. 100°-103° C.

Workup

  1. additionTo a suspension of 1.8 g
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux
  4. temperatureheating
  5. filtrationAt this time the reaction mixture is filtered
  6. customto remove insoluble material
  7. customevaporated to dryness
  8. customThe product is purified
  9. customThe desired fraction was evaporated to dryness
  10. customtriturated with ether
  11. customto give 120 mg

Sources & evidence

ORD record
ord-33d63e5c425c4842825c98d7812a539a
Source dataset
uspto-grants-1984_12
Patent number
US04490527

Reaction notes

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