Benzene → HCID 19787190, compound

HRID 1885199Notes

Reaction equation

HRID 1885199 reaction equation
[C:1]([O:4][C:5]1[C:13]([CH3:14])=[CH:12][C:8](C(O)=O)=[CH:7][C:6]=1[CH3:15])(=[O:3])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])C=CC=CC=1.C1C=CC=CC=1.C([N:41]([CH2:44]C)CC)C>>[C:1]([O:4][C:5]1[C:6]([CH3:15])=[CH:7][C:8]([N:41]=[C:44]=[O:23])=[CH:12][C:13]=1[CH3:14])(=[O:3])[CH3:2]

Participants

5

Reactant 4

HCID 241BenzeneHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 187041893,5-Dimethyl-4-acetoxybenzoic acid

Product 1

HCID 19787190HCID 19787190, compound

Procedure

To a mixture of 4-acetoxy-3,5-dimethylbenzoic acid (270 mg), diphenylphosphoryl azide (DPPA, 430 mg) and benzene (6 ml) was added dropwise triethylamine (0.18 ml) and the mixture was stirred at room temperature for 30 minutes and then at reflux for 40 minutes to obtain a solution of 4-acetoxy-3,5-dimethylphenylisocyanate. To the solution was added 5-amino-2-ethyl-4-(2-methoxyphenyl)-thieno[2,3-b]pyridine (284 mg) and the mixture was heated under reflux for 5 hours. The mixture was washed with water and dried over MgSO4 and the solvent was distilled off. To the residue was added ethanol to obtain N-(4-acetoxy-3,5-dimethylphenyl)-N'-[2-ethyl-4-(2-methoxyphenyl)thien[2,3-b]pyridin-5-yl]urea (350 mg, 71.6%) as crystals. The crystals were recrystallized from ethanol to obtain colorless needles, mp: 217°-218° C.

Workup

  1. temperatureat reflux for 40 minutes

Sources & evidence

ORD record
ord-2261ed02f9c646d187e05c46ba6e14eb
Source dataset
uspto-grants-1992_09
Patent number
US05143919

Reaction notes

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