Cysteamine Hydrochloride → HCID 20213304, compound

HRID 65740Notes

Reaction equation

HRID 65740 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][SH:5].CC(C)([O-])C.[K+].C(O[CH2:16][C:17]1[O:18][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][N:26]([CH3:28])[CH3:27])=[CH:20][CH:21]=1)(=O)C>CN(C)C=O.CO>[CH3:28][N:26]([CH3:27])[CH2:25][CH2:24][CH2:23][CH2:22][C:19]1[O:18][C:17]([CH2:16][S:5][CH2:4][CH2:3][NH2:2])=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 9082Cysteamine HydrochlorideHCID 23452115[5-[4-(Dimethylamino)butyl]-2-furanyl]methyl ethanoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 20213304HCID 20213304, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

Cysteamine hydrochloride (4.5 g) was added to a cooled solution of potassium-t-butoxide (8.98 g) in dry dimethylformamide (125 ml). The mixture was stirred for 20 min and [5-[4-(dimethylamino)butyl]-2-furanyl]methyl ethanoate (9.6 g) was added. The reaction was heated at 90° for 4 hr, poured onto an ice-water mixture and extracted with chloroform. Distillation of the organic extract gave a yellow oil which after column chromatography on silica, using methanol/0.880 ammonia (9:1) as eluent, and a further distillation afforded a colourless oil b.p. 140°/0.05 mm Hg. Found: C, 60.81; H, 9.86; N, 10.44. Calc. for C13H24N2OS: C, 60.91; H, 9.44; N, 10.93%.

Workup

  1. temperatureThe reaction was heated at 90° for 4 hr
  2. extractionextracted with chloroform
  3. distillationDistillation of the
  4. extractionorganic extract
  5. customgave a yellow oil which after column chromatography on silica
  6. distillationa further distillation

Sources & evidence

ORD record
ord-3fbcb9616b764f8b86c0f958fa12c163
Source dataset
uspto-grants-1978_12
Patent number
US04128658

Reaction notes

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