Formaldehyde → HCID 21394499, compound

HRID 460774Notes

Reaction equation

HRID 460774 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][S:6](=[O:9])(=[O:8])[CH2:5][C:4]([CH3:11])([CH3:10])[NH:3]1.[C-:13]#[N:14].[K+].[CH2:16]=O>Cl>[C:13]([CH2:16][N:3]1[C:2]([CH3:12])([CH3:1])[CH2:7][S:6](=[O:9])(=[O:8])[CH2:5][C:4]1([CH3:11])[CH3:10])#[N:14]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 9032Potassium CyanideHCID 21394477HCID 21394477, compound

Product 1

HCID 21394499HCID 21394499, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
45 °C

Procedure

19.1 g (0.1 mole) of 2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide is added, with ice cooling, to 20 ml of 5N hydrochloric acid; 6.5 g of potassium cyanide is added and then in ca. 20 minutes, with good stirring, an addition made dropwise of 12.5 g of a 30% formaldehyde solution. The reaction mixture is subsequently stirred for 15 hours at 45° C. After cooling, the precipitate is filtered off under suction, washed with water, dried, and recrystallised from toluene/hexane to obtain 1-cyanomethyl-2,2,6,6-tetramethyl-1-aza-4-thiacyclohexane-4,4-dioxide (11), M.P. 188° C.

Workup

  1. additionwith good stirring, an addition
  2. temperatureAfter cooling
  3. filtrationthe precipitate is filtered off under suction
  4. washwashed with water
  5. customdried
  6. customrecrystallised from toluene/hexane

Sources & evidence

ORD record
ord-ec25f525ffca4c5fa6cab510ea0dd86e
Source dataset
uspto-grants-1977_12
Patent number
US04061631

Reaction notes

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