Acetic Anhydride → HCID 12666260, compound

HRID 1355707Notes

Reaction equation

HRID 1355707 reaction equation
[CH3:1][CH2:2][O:3][C:4](OCC)(OCC)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[N:17]#[C:18][NH2:19].C(OC(=O)C)(=O)C>C(OCC)(=O)C>[CH2:2]([O:3][C:4]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[N:19][C:18]#[N:17])[CH3:1]

Participants

5

Reactant 3

HCID 7918Acetic Anhydride2×HCID 9864CyanamideHCID 74268Benzene, (triethoxymethyl)-

Product 1

HCID 12666260HCID 12666260, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Following the method of Huffmann and Schaefer (J. Org. Chem. 1963, 28, 1816), a stirred mixture of 50 ml (221 mmol) triethylorthobenzoate, 9.3 g (221 mmol) cyanamide and 42 ml (442 mmol) acetic anhydride was heated at 130-150° C. for 1.5 hours with concomitant removal of the ensuing ethyl acetate and acetic anhydride by distillation from the reaction flask. The reaction mixture was then concentrated in vacuo using a rotary evaporater. Kugelrohr distillation (120° C., 3 mbar) afforded 35.8 g (93%) N-cyano-benzenecarboximidic acid ethyl ester as a colourless oil. ES-MS m/e (%): 175 (M+H+, 100).

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. distillationKugelrohr distillation (120° C., 3 mbar)

Sources & evidence

ORD record
ord-a06b16e63b004876a714ee900ee81851
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

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