O-Toluidine → HCID 44416088, compound

HRID 2264240Notes

Reaction equation

HRID 2264240 reaction equation
[NH2:1][C:2]1[C:3]([CH3:8])=[CH:4][CH:5]=[CH:6][CH:7]=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>>[NH:18]1[C:22]2=[N:23][CH:24]=[CH:25][CH:26]=[C:21]2[C:20]([C:27]2[CH:32]=[CH:31][N:30]=[C:29]([NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[CH3:8])[N:28]=2)=[CH:19]1

Participants

3

Reactant 2

HCID 7242O-ToluidineHCID 59596028HCID 59596028, compound

Product 1

HCID 44416088HCID 44416088, compoundYield 33.2%

Procedure

Using the procedure of example 1, o-toluidine (87 mg) was reacted with compound 1f (100 mg) to provide compound 8 (27 mg, 33%). 1H NMR (400 MHz, CD3OD) δ 8.55 (d, J=8.0 Hz, 1H), 8.24 (d, J=5.2 Hz, 1H), 8.12 (s, 1H), 7.69 (d, J=7.6 Hz, 1H), 7.29 (q, J=7.6 Hz, 1H), 7.18 (d, J=7.2 Hz, 1H), 7.11 (d, J=5.6 Hz, 1H), 7.11 (dd, J=7.6 Hz, 4.8 Hz, 1H), 2.35 (s, 3H). MS (ESI) m/z: 302 (M+H)+.

Sources & evidence

ORD record
ord-c8b75e30b27f4540a87330117ce460ba
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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