Benzoyl isocyanate → N-(6-cyanobenzo[d][1,3]dioxol-5-ylcarbamoyl)benzamide

HRID 44391Notes

Reaction equation

HRID 44391 reaction equation
[NH2:1][C:2]1[C:3]([C:11]#[N:12])=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.[C:13]([N:21]=[C:22]=[O:23])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>>[C:11]([C:3]1[C:2]([NH:1][C:22]([NH:21][C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:23])=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)#[N:12]

Participants

3

Reactant 2

HCID 78210Benzoyl isocyanateHCID 6879796-Amino-1,3-benzodioxole-5-carbonitrile

Product 1

HCID 57456931N-(6-cyanobenzo[d][1,3]dioxol-5-ylcarbamoyl)benzamide

Procedure

Prepared as in Example 53a from 6-aminobenzo[d][1,3]dioxole-5-carbonitrile and benzoyl isocyanate as a yellow solid (157 mg, 82%). 1H NMR (400 MHz, DMSO-d6) δ6.19 (s, 2H), 7.42 (s, 1H), 7.54 (t, J=8 Hz, 2H), 7.66 (t, J=7.6 Hz, 1H), 7.74 (s, 1H), 8.03 (d, J=9.2 Hz, 2H), 11.32 (d, J=12.8 Hz, 2H). MS 309 (MH+).

Sources & evidence

ORD record
ord-9381df6233714bc1a101c664999a5d74
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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