Acetic Anhydride → HCID 18432836, compound

HRID 2288658Notes

Reaction equation

HRID 2288658 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:25]=[CH:24][C:18]([CH2:19][NH:20][C:21]([NH2:23])=[O:22])=[CH:17][CH:16]=1>C1(C)C=CC=CC=1>[Cl:14][C:15]1[CH:25]=[CH:24][C:18]([CH2:19][NH:20][C:21]([NH:23][C:4](=[O:6])[CH2:3][C:1]#[N:2])=[O:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 9740Cyanoacetic acidHCID 1484508HCID 1484508, compound

Product 1

HCID 18432836HCID 18432836, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

68.7 g of 98% cyanoacetic acid and 155 ml of acetic anhydride were kept at 65° C. for 30 minutes. 4-chlorobenzylurea (132.9 g) was added in portions over 10 minutes. After 2 hr at 70-75° C., further acetic anhydride (25 ml) was added. After a further 15 minutes, 90 ml of toluene was added, cooled to room temperature, the solid collected and washed with toluene to give the title compound (155.60 g) as a white solid mp 203-6° C.

Workup

  1. waitAfter a further 15 minutes
  2. customthe solid collected
  3. washwashed with toluene

Sources & evidence

ORD record
ord-938585194d4f4ed8bdd4dee226156850
Source dataset
uspto-grants-2000_07
Patent number
US06090816

Reaction notes

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