HCID 21394464, compound → HCID 21394504, compound

HRID 460773Notes

Reaction equation

HRID 460773 reaction equation
[N:1]([N:3]1[C:8]([CH3:10])([CH3:9])[CH2:7][S:6](=[O:12])(=[O:11])[CH2:5][C:4]1([CH3:14])[CH3:13])=O>C(O)(=O)C.O.[Zn]>[NH2:1][N:3]1[C:4]([CH3:13])([CH3:14])[CH2:5][S:6](=[O:12])(=[O:11])[CH2:7][C:8]1([CH3:10])[CH3:9]

Participants

5

Reactant 1

HCID 21394464HCID 21394464, compound

Product 1

HCID 21394504HCID 21394504, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

22.0 g (0.1 mole) of 1-nitroso-2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide is suspended in a mixture of 150 ml of glacial acetic acid and 100 ml of water. Within 3 hours, 40 g of zinc dust is introduced in small portions, the temperature being maintained between 30° and 35° C. The reaction mixture is subsequently fully stirred for 5 hours at 50° C; the zinc sediment is filtered off hot, and the cooled filtrate rendered alkaline with sodium hydroxide solution. It is extracted with ether, the ether solution dried over sodium sulphate, and the solvent evaporated off. Crystallisation of the residue from ligroin yields 1-amino-2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide (10), M.P. 122° C.

Workup

  1. temperaturethe temperature being maintained between 30° and 35° C
  2. filtrationthe zinc sediment is filtered off hot
  3. extractionIt is extracted with ether
  4. dry with materialthe ether solution dried over sodium sulphate
  5. customthe solvent evaporated off
  6. customCrystallisation of the residue from ligroin

Sources & evidence

ORD record
ord-651d583ed6ed43e58d11318332852cb9
Source dataset
uspto-grants-1977_12
Patent number
US04061631

Reaction notes

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