P-Phenylenediamine → HCID 58692237, compound

HRID 2264260Notes

Reaction equation

HRID 2264260 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.C1(S([N:18]2[C:22]3=[N:23][CH:24]=[CH:25][CH:26]=[C:21]3[C:20]([C:27]3[CH:32]=[CH:31][N:30]=[C:29](Cl)[N:28]=3)=[CH:19]2)(=O)=O)C=CC=CC=1>>[NH2:7][C:4]1[CH:5]=[CH:6][C:1]([NH:8][C:29]2[N:28]=[C:27]([C:20]3[C:21]4[C:22](=[N:23][CH:24]=[CH:25][CH:26]=4)[NH:18][CH:19]=3)[CH:32]=[CH:31][N:30]=2)=[CH:2][CH:3]=1

Participants

3

Reactant 2

HCID 7814P-PhenylenediamineHCID 59596028HCID 59596028, compound

Product 1

HCID 58692237HCID 58692237, compoundYield 49.1%

Procedure

Using the procedure of example 1, 1,4-phenylenediamine (175 mg) was reacted with compound 1f (100 mg) to provide compound 37 (40 mg, 25%). 1H NMR (400 MHz, CD3OD) δ 8.43 (d, J=8.0 Hz, 1H), 8.23 (d, J=8.0 Hz, 1H), 8.20 (s, 1H), 8.18 (d, J=4.8 Hz, 1H), 7.36 (m, 1H), 7.33 (d, J=8.0 Hz, 1H), 7.18 (dd, J=8.0 Hz, 5.6 Hz, 1H), 7.11 (d, J=5.2 Hz, 1H), 6.84 (d, J=8.0 Hz, 1H), 6.80 (d, J=8.0 Hz, 1H). MS (ESI) m/z: 301 (M+H)+.

Sources & evidence

ORD record
ord-f0949bb7732d4a2a934eb37cf019099b
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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