N,N-dimethyl-p-phenylenediamine → HCID 58692251, compound

HRID 2264261Notes

Reaction equation

HRID 2264261 reaction equation
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.C1(S([N:20]2[C:24]3=[N:25][CH:26]=[CH:27][CH:28]=[C:23]3[C:22]([C:29]3[CH:34]=[CH:33][N:32]=[C:31](Cl)[N:30]=3)=[CH:21]2)(=O)=O)C=CC=CC=1>>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:31]2[N:30]=[C:29]([C:22]3[C:23]4[C:24](=[N:25][CH:26]=[CH:27][CH:28]=4)[NH:20][CH:21]=3)[CH:34]=[CH:33][N:32]=2)=[CH:5][CH:4]=1

Participants

3

Reactant 2

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 59596028HCID 59596028, compound

Product 1

HCID 58692251HCID 58692251, compoundYield 58.4%

Procedure

Using the procedure of example 1, N,N-dimethyl-p-phenylenediamine (221 mg) was reacted with compound 1f (100 mg) to provide compound 38 (52 mg, 29%). 1H NMR (400 MHz, CD3OD) δ 8.85 (d, J=8.0 Hz, 1H), 8.25 (d, J=8.0 Hz, 1H), 8.20 (s, 1H), 8.18 (d, J=4.8 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.43 (m, 1H), 7.18 (dd, J=8;0 Hz, 5.6 Hz, 1H), 7.12 (d, J=5.6 Hz, 1H), 6.88 (d, J=8.0 Hz, 1H), 6.85 (d, J=8.0 Hz, 1H), 2.90 (s, 6H).

Sources & evidence

ORD record
ord-ae712d41b0a84f228217bf3ba1d8d45c
Source dataset
uspto-grants-2010_12
Patent number
US07855205B2

Reaction notes

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