1-Iodo-4-isocyanatobenzene → tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazate

HRID 22638Notes

Reaction equation

HRID 22638 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:9]([NH:17][CH2:18][CH2:19][CH3:20])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[I:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([N:9]([N:17]([C:29]([NH:28][C:25]2[CH:26]=[CH:27][C:22]([I:21])=[CH:23][CH:24]=2)=[O:30])[CH2:18][CH2:19][CH3:20])[C:10]([O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 33997871-Iodo-4-isocyanatobenzeneHCID 22591495tert-Butyl 2-(3-cyanophenyl)-3-propylcarbazate

Product 1

HCID 11191609tert-Butyl 2-(3-cyanophenyl)-3-(4-iodophenylaminocarbonyl)-3-propylcarbazateYield 84.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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.

Sources & evidence

ORD record
ord-b11fe237dcff4b788461ffd92d003266
Source dataset
uspto-grants-2005_02
Patent number
US06849626B2

Reaction notes

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