Reaction #50916

ord-b11fe237dcff4b788461ffd92d003266

Reaction equation

CCCNN(C(=O)OC(C)(C)C)c1cccc(C#N)c1
404
CCCNN(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-propylcarbazate
O=C=Nc1ccc(I)cc1
4-iodophenyl isocyanate
→
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
405
Yield 84.7%
CCCN(C(=O)Nc1ccc(I)cc1)N(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate
Yield 84.7%

Reactants

CCCNN(C(=O)OC(C)(C)C)c1cccc(C#N)c1
404
CCCNN(C(=O)OC(C)(C)C)c1cccc(C#N)c1
tert-Butyl 2-(3-cyanophenyl)-3-propylcarbazate
O=C=Nc1ccc(I)cc1
4-iodophenyl isocyanate

Reagents

None

Solvents

c1ccncc1
pyridine

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

2.0 g (7.273 mmol) of 404 are stirred at RT for 1.5 h in 5.0 ml of pyridine with 1.78 g (7.265 mmol) of 4-iodophenyl isocyanate. After customary work-up, 3.2 g (84.7%) of 405 are thus obtained as crystals having a melting point of 184-185° C.; MS(FAB)=521.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06849626B2uspto-grants-2005_02