Ammonia → Carbamimidoyl-nitroso-acetic acid ethyl ester

HRID 444920Notes

Reaction equation

HRID 444920 reaction equation
[NH3:1].C(O)C.Cl.[CH2:6]([O:8][C:9]([CH2:11][C:12](=[NH:16])OCC)=[O:10])[CH3:7].[N:17]([O-:19])=O.[Na+].O.Cl>>[CH2:6]([O:8][C:9](=[O:10])[CH:11]([C:12](=[NH:16])[NH2:1])[N:17]=[O:19])[CH3:7]

Participants

7

Reactant 6

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 702EthanolHCID 962WaterHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 23668193Sodium Nitrite

Product 1

HCID 12439904Carbamimidoyl-nitroso-acetic acid ethyl ester

Procedure

To a solution of 2M ammonia in Ethanol (152 ml, 0.304 mmol) at 0° C. to 5° C., ethyl ethoxycarbonylacetimidate HCl (25 g, 0.127 mmol) was added over 30 minutes. The reaction was stirred vigorously at this temperature for 3 hours, after which a solution of sodium nitrite in water (9.63 g, 0.139 mmol) was added in a single portion. The pH of the mixture was adjusted to pH6 with the addition of 5N HCl. The reaction mixture was left to stir at RT overnight. The yellow precipitate formed was filtered under vacuum, washed with water and dried to give the title compound;

Workup

  1. waitThe reaction mixture was left
  2. stirringto stir at RT overnight
  3. customThe yellow precipitate formed
  4. filtrationwas filtered under vacuum
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-67123abd9fd54f8eb5ea1476edf0338f
Source dataset
uspto-grants-2013_07
Patent number
US08476269B2

Reaction notes

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