Hydrochloric Acid → HCID 178479105, compound

HRID 1084785Notes

Reaction equation

HRID 1084785 reaction equation
[ClH:1].C([N:6]([CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[OH:14])[NH2:7])(C)(C)C.[C-:15]#[N:16].[Na+].[CH2:18]=O.Cl.[N:21]([O-:23])=O.[Na+]>O>[ClH:1].[OH:14][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH:8]1[NH:6][N+:7]1[N-:21][O:23][C:15](=[NH:16])[CH:18]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8929Sodium CyanideHCID 14795576N-tert.-Butyl-N-(2-hydroxycyclohexyl)-hydrazine hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 178479105HCID 178479105, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 13.35 g of N-tert.-butyl-N-(2-hydroxycyclohexyl)-hydrazine hydrochloride, 3.1 g of sodium cyanide and 50 ml of water is stirred in an ice bath and a 39% strength formalin solution (5.7 g) is added dropwise. The pH of the mixture is brought to 7 to 7.5 and the mixture is stirred at room temperature for 3 hours. The pH is then brought to 1 with concentrated hydrochloric acid and a solution of 6 g of sodium nitrite in 25 ml of water is added dropwise. After one hour, the nitroso compound is extracted with diethyl ether, the ethereal phase is dried and ethereal HCl is added. After 2 days, the precipitate is filtered off with suction and recrystallized from isopropanol/ethyl acetate. Yield: 4.5 g melting point: 174°-5° C. (decomp.)

Workup

  1. stirringthe mixture is stirred at room temperature for 3 hours
  2. extractionthe nitroso compound is extracted with diethyl ether
  3. customthe ethereal phase is dried
  4. additionethereal HCl is added
  5. waitAfter 2 days
  6. filtrationthe precipitate is filtered off with suction
  7. customrecrystallized from isopropanol/ethyl acetate

Sources & evidence

ORD record
ord-efdfb5fc9141422f92b8d9d82a883350
Source dataset
uspto-grants-1991_04
Patent number
US05006540

Reaction notes

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