m-Toluidine → HCID 44416107, compound

HRID 2264241Notes

Reaction equation

HRID 2264241 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[CH:3]=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:3]=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=3)[N:28]=2)=[CH:19]1

Participants

3

Reactant 2

HCID 7934m-ToluidineHCID 59596028HCID 59596028, compound

Product 1

HCID 44416107HCID 44416107, compoundYield 46%

Procedure

Using the procedure of example 1, m-toluidine (87 mg) was reacted with compound 1f (100 mg) to provide compound 9 (37 mg, 46%). 1H NMR (400 MHz, CD3OD) δ 8.90 (d, J=8;0 Hz, 1H), 8.30 (m, 2H), 8.18 (s, 1H), 7.63 (s, 1H), 7.43(d, J=8.0 Hz, 1H), 7.27 (d, J=7.6 Hz, 1H), 7.22 (m, 1H), 7.17 (d, J=5.2 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 2.42 (s, 3H). MS (ESI) m/z: 302 (M+H)+.

Sources & evidence

ORD record
ord-4037708c7f7c43dab0aa07c3984783cb
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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