Ammonia → HCID 45092056, compound

HRID 2294681Notes

Reaction equation

HRID 2294681 reaction equation
C([S:8][C:9]([CH3:20])([CH3:19])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])C1C=CC=CC=1.N.[Na]>CCOCC>[CH3:20][C:9]([SH:8])([CH3:19])[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 5360545SodiumHCID 67723796HCID 67723796, compound

Product 1

HCID 45092056HCID 45092056, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

3.49 g (11.8 mmol) of tert-butyl [2-(benzylthio)-2-methylpropyl]carbamate dissolved in 10 ml of ether are placed in a flask which is fitted with an ammonia condenser and a gas inlet. The solution is cooled to -78°, thereafter about 35 ml of ammonia are condensed in. Sodium (about 1 g) in small pieces is added to this solution until the blue colour of the solution persists. The mixture is allowed to warm slowly, the excess sodium is destroyed by the addition of ammonium chloride (about 3.5 g) and the ammonia is blown off using nitrogen. The residue is partitioned between 50 ml of water and 250 ml of ether. The organic phase is separated, dried over sodium sulphate and evaporated. There are obtained 2.29 g of tert-butyl [2-methyl-2-mercaptopropyl]carbamate as a colourless solid; MS: 149 (M-C4H8)+.

Workup

  1. customare placed in a flask
  2. customwhich is fitted with an ammonia condenser and a gas inlet
  3. temperatureThe solution is cooled to -78°
  4. customcondensed in
  5. temperatureto warm slowly
  6. customthe excess sodium is destroyed by the addition of ammonium chloride (about 3.5 g)
  7. customThe residue is partitioned between 50 ml of water and 250 ml of ether
  8. customThe organic phase is separated
  9. dry with materialdried over sodium sulphate
  10. customevaporated

Sources & evidence

ORD record
ord-b5d4c16e3da549918666a2e4561425d9
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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