Ethanol → HCID 13254214, compound

HRID 905262Notes

Reaction equation

HRID 905262 reaction equation
[CH2:1]([NH:5][C:6]([NH:8][CH2:9][CH2:10][Cl:11])=[O:7])[CH:2]([CH3:4])[CH3:3].C(O)C.[N:15]([O-])=[O:16].[Na+]>Cl.O>[CH2:1]([NH:5][C:6]([N:8]([CH2:9][CH2:10][Cl:11])[N:15]=[O:16])=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 702EthanolHCID 13254213HCID 13254213, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 13254214HCID 13254214, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

A 2 g (11.2 mmol) quantity of 1-isobutyl-3-(2-chloroethyl) urea was dissolved in 25 ml of concentrated HCl:ethanol, 2:1, and cooled to 5° C. A solution of 773 mg (11.2 mmol) of sodium nitrite in 5 ml of water was added in portions and the mixture was stirred at this temperature for 2 hrs. The crystalline yellow solid was filtered and dried in vacuo overnight giving 1.6 g (70%) of the product, MP 51° C. (decomposes). IR analysis showed peaks at 1705/cm (C=O) and 1525/cm (C--N=O). NMR: Doublet (6H, J=6.8 Hz) at 0.9 ppm, multiplet (1H) at 2.0 ppm, multiplet (6H) at 3.7 ppm.

Workup

  1. filtrationThe crystalline yellow solid was filtered
  2. customdried in vacuo overnight

Sources & evidence

ORD record
ord-44ea6bfb58004539b495f420b12d7cf3
Source dataset
uspto-grants-1983_12
Patent number
US04423076

Reaction notes

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