3-Isocyanatobenzonitrile → HCID 22318902, compound

HRID 497307Notes

Reaction equation

[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:12][CH:11]=2)=[O:7])=[CH:4][CH:3]=1.[C:22]([C:24]1[CH:25]=[C:26]([N:30]=[C:31]=[O:32])[CH:27]=[CH:28][CH:29]=1)#[N:23]>CC(N(C)C)=O.C(Cl)Cl>[C:22]([C:24]1[CH:25]=[C:26]([NH:30][C:31](=[O:32])[NH:1][C:2]2[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][C:13]([S:16](=[O:19])(=[O:18])[NH2:17])=[CH:12][CH:11]=3)=[O:7])=[CH:4][CH:3]=2)[CH:27]=[CH:28][CH:29]=1)#[N:23]

Participants

Conditions

Temperature: 0 °C

Procedure

4-Amino-N-(4-sulfamoylbenzyl)-benzamide (2.13 g, 1 eq.) was dissolved anhydrous in DMA (10 ml) under inert atmosphere, anhydrous DCM (30 ml) was added and the solution was cooled to 0° C. A solution of 3-cyanophenylisocyanate (1.9 g, 1.9 eq.) in anhydrous DCM (10 ml) was added and the mixture stirred over night. The resulting precipitate was filtered off, washed with methanol and dried in vacuo to yield 2.38 g (76%) 4-[3-(3-cyanophenyl)-ureido]-N-(4-sulfamoylbenzyl)-benzamide.

Workup

additionwas added
filtrationThe resulting precipitate was filtered off
washwashed with methanol
customdried in vacuo

Sources & evidence

ORD record: ord-620a552af3734e3e868315ec63497fe4
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06949567B2

Reaction notes

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