Oxalyl chloride → HCID 23370021, compound

HRID 1900880Notes

Reaction equation

HRID 1900880 reaction equation
[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][N:4]=1)#[N:2].C(Cl)(=O)[C:13](Cl)=[O:14]>ClCCCl>[C:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([N:9]=[C:13]=[O:14])=[O:8])=[CH:5][N:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 37537876-Cyanonicotinamide

Product 1

HCID 23370021HCID 23370021, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 6-cyanonicotinamide (Synthesis (1983), 316) (1.2 g) in 1,2-dichloroethane (28 ml) was added oxalyl chloride (1.3 ml) and the mixture was heated at reflux with stirring for 2.5 hours. The reaction mixture was cooled and the solvents were removed in vacuo to yield 6-cyanonicotinoyl isocyanate as a yellow solid residue. Then in a similar manner to Example 1, starting material step (a), this residue, t-butyl 4-aminophenoxyacetate, acetate salt (1.59 g), triethylamine (3.8 ml) and acetonitrile (140 ml total) gave, after stirring at ambient temperature for 3 hours followed by evaporation of the solvents, a yellow solid, which was collected, washed with cold acetonitrile and with hexane and dried to give t-butyl 4-[3-(6-cyanopyrid-3-ylcarbonyl)ureido]phenoxyacetate (2.37 g): m.p. 220°-222° C. (decomposes); NMR Spectrum (DMSO-d6) 1.48 (9H, s), 4.67 (2H, s), 6.94 (2H, d), 7.52 (2H, d), 8.27 (1H, d), 8.58 (1H, dd), 9.25 (1H, d), 10.41 (1H, s), 11.40 (1H, s); Mass Spectrum m/Z 396 (M+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. temperatureThe reaction mixture was cooled
  4. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-a2b1b8bf36aa424f9325a6b40ef1578d
Source dataset
uspto-grants-1996_11
Patent number
US05576334

Reaction notes

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