Ethanol → HCID 13254211, compound

HRID 905259Notes

Reaction equation

HRID 905259 reaction equation
[CH2:1]([NH:7][C:8]([NH:10][CH2:11][CH2:12][Cl:13])=[O:9])[CH2:2][C:3]([CH3:6])([CH3:5])[CH3:4].C(O)C.[N:17]([O-])=[O:18].[Na+]>Cl.O>[CH2:1]([NH:7][C:8]([N:10]([CH2:11][CH2:12][Cl:13])[N:17]=[O:18])=[O:9])[CH2:2][C:3]([CH3:6])([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 702EthanolHCID 13254210HCID 13254210, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13254211HCID 13254211, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A 2.07 g (10 mmol) quantity of 1-neohexyl-3-(2-chloroethyl) urea was dissolved in 15 ml of concentrated HCl:ethanol, 2:1, at 10° C., and 690 mg (10 mmol) sodium nitrite dissolved in 3 ml of water was added. Stirring at 5° C. continued for 1.5 hrs. and the precipitate was washed with four 25 ml portions of distilled water. After drying in vacuo overnight, 1.7 g (74%) of the product was obtained which melted at 43.0°-43.5° C. (decomposes). IR analysis showed peaks at 1705/cm (C=O) and 1525/cm (C--N=O). NMR: singlet (9H) at 0.9 ppm, multiplet (2H) at 1.3 ppm, symmetrical multiplet (6H) at 3.8 ppm. No evidence of isomeric material was detected.

Workup

  1. additionwas added
  2. washand the precipitate was washed with four 25 ml portions of distilled water
  3. customAfter drying in vacuo overnight

Sources & evidence

ORD record
ord-908605765dd244858a273541dec2315d
Source dataset
uspto-grants-1983_12
Patent number
US04423076

Reaction notes

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