Acetic Anhydride → 1-(3-Chlorobenzyl)-3-cyanoacetyl-urea

HRID 2305385Notes

Reaction equation

HRID 2305385 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].C(OC(=O)C)(=O)C.[Cl:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[CH2:18][NH:19][C:20]([NH2:22])=[O:21]>C1COCC1>[Cl:14][C:15]1[CH:16]=[C:17]([CH:23]=[CH:24][CH:25]=1)[CH2:18][NH:19][C:20]([NH:22][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[O:21]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 27325773-Chlorobenzylurea

Product 1

HCID 184328351-(3-Chlorobenzyl)-3-cyanoacetyl-ureaYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.76 g of 98% cyanoacetic acid and 14 ml of acetic anhydride were heated for 1 hour at 65° C. A solution of 7.73 g of (3-chlorobenzyl)urea in 55 ml THF was added and the mixture kept for 4 hours at 65° C. The THF was removed in vacuo and the residue diluted with 50 ml of toluene. The solid was collected and washed to give the title compound (8.94 g) as a white solid.

Workup

  1. customThe THF was removed in vacuo
  2. additionthe residue diluted with 50 ml of toluene
  3. customThe solid was collected
  4. washwashed

Sources & evidence

ORD record
ord-ccda60fe1c8541dc88dd66c6905baf56
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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