O-Phenylenediamine → HCID 54475342, compound

HRID 1839442Notes

Reaction equation

HRID 1839442 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[C:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14](Cl)=[O:15])#[N:10]>C(N(CC)CC)C>[C:9]([C:11]1[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=1)[C:14]([NH:7][C:2]1[C:1]([NH:8][C:14](=[O:15])[C:13]2[CH:17]=[CH:18][CH:19]=[C:11]([C:9]#[N:10])[CH:12]=2)=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])#[N:10]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 3084833-Cyanobenzoyl chloride

Product 1

HCID 54475342HCID 54475342, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Using a procedure similar to Example 1D, except starting with 1,2-benzenediamine and 3-cyanobenzoyl chloride with triethylamine as base, the title compound was obtained as an off-white solid (18%); IR(KBr): 3362, 2238, 1656, 1552 cm−1; NMR(300 MHz, DMSO-d6): 7.33 (m,2H); 7.64 (m, 2H); 7.73 (t, 2H, J=9.5 Hz); 8.05 (d, 2H, J=9.3 Hz); 8.24 (d, 2H, J=9.9 Hz); 8.35 (s, 2H); 10.18 (br s, 2H); MS(FD): 366.1.

Sources & evidence

ORD record
ord-2ee57f26ab334541a112c4621f64ed1b
Source dataset
uspto-grants-2004_01
Patent number
US06677369B2

Reaction notes

Loading…