Ethyl isocyanate → HCID 47448393, compound

HRID 131674Notes

Reaction equation

HRID 131674 reaction equation
Cl.[N+](C1C=C(C=CC=1)CN)([O-])=O.[CH2:13]([NH:15][C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1)=[O:17])[CH3:14].C(N(CC)CC)C.C(N=C=O)C>C1COCC1>[CH2:13]([NH:15][C:16]([NH:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-:28])=[O:27])[CH:21]=1)=[O:17])[CH3:14]

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 8471TriethylamineHCID 86760688HCID 86760688, compound

Product 1

HCID 47448393HCID 47448393, compoundYield 98.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Ethyl-N′-(3-nitrobenzyl)urea 3-Nitrobenzylamine hydrochloride (754 mg, 4.0 mmol) and triethylamine (404 mg, 4 mmol) were stirred in THF (10 ml) for 15 min in an ice bath. Ethylisocyanate (335 μl, 4.23 mmol) was added dropwise to the solution and the reaction allowed to stand at room temperature for 2 h after addition was complete. The reaction was partitioned between ethyl acetate (30 ml) and water (30 ml). The organic phase was washed with water, brine and dried (sodium sulphate). The solvent was evaporated under vacuum to give N-ethyl-N′-(3-nitrobenzyl)urea (880 mg). Rf; DCM/methanol (10:1) 0.40.

Workup

  1. additionafter addition
  2. customThe reaction was partitioned between ethyl acetate (30 ml) and water (30 ml)
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried (sodium sulphate)
  5. customThe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-315c8e9751e847c48e13394ebe10f731
Source dataset
uspto-grants-2008_06
Patent number
US07384963B2

Reaction notes

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