Ethanol → HCID 13278824, compound

HRID 1902802Notes

Reaction equation

HRID 1902802 reaction equation
C(N(CC)CC)C.[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH2:18])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(O)C.[CH3:22]I.[C:24](=[S:26])=[S:25]>>[C:8]([O:12][C:13]([NH:15][CH2:16][CH2:17][NH:18][C:24](=[S:26])[S:25][CH3:22])=[O:14])([CH3:11])([CH3:10])[CH3:9]

Participants

6

Reactant 5

HCID 702EthanolHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 187201N-BOC-ethylenediamine

Product 1

HCID 13278824HCID 13278824, compound

Conditions

Temperature
22 °C

Procedure

Triethylamine (15.5 cc) is added to a solution of 2-tert.-butoxycarbonylamino-ethylamine (17.62 g) in 95% strength ethanol (110 cc), and carbon disulphide (6.65 cc) is introduced dropwise in the course of 10 minutes, whilst maintaining the temperature at between 20° C. and 25° C. The mixture is stirred for 1 hour 30 minutes at 22° C. Methyl iodide (6.85 cc) is then added and the mixture is stirred for 1 hour 30 minutes at 22° C. It is then concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa), the residue is taken up in ethyl acetate (200 cc), and the organic phase is washed with water (3×100 cc), dried over sodium sulphate, filtered and concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa). Methyl N-(2-tert.-butoxycarbonylamino-ethyl)-dithiocarbamate (23.2 g) is obtained in the form of a yellow oil.

Workup

  1. additionis introduced dropwise in the course of 10 minutes
  2. temperaturewhilst maintaining the temperature at between 20° C. and 25° C
  3. stirringthe mixture is stirred for 1 hour 30 minutes at 22° C
  4. concentrationIt is then concentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)
  5. washthe organic phase is washed with water (3×100 cc)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness at 20° C. under 20 mm Hg (2.7 kPa)

Sources & evidence

ORD record
ord-8680553970524a7185719749eebd233b
Source dataset
uspto-grants-1982_12
Patent number
US04365062

Reaction notes

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