4-Aminophenol → HCID 58692226, compound

HRID 2264262Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][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>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][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:3][CH:4]=1

Participants

Reactant 2

HCID 4034-Aminophenol

HCID 59596028HCID 59596028, compound

Product 1

HCID 58692226HCID 58692226, compoundYield 29.3%

Procedure

Using the procedure of example 1, 4-aminophenol (177 mg) was reacted with compound 1f (200 mg) to provide compound 39 (48 mg, 29%). 1H NMR (400 MHz, CD3OD) δ 8.48 (d, J=8.0 Hz, 1H), 8.24 (s, 1H), 8.23 (d, J=8.0 Hz, 1H), 8.12 (d, J=4.8 Hz, 1H), 7.45 (d, J=8.0 Hz, 1H), 7.05 (dd, J=8.0 Hz, 5.6 Hz, 1H), 7.00 (d, J=5.2 Hz, 1H), 6.98 (m, 1H), 6.85 (d, J=8.0 Hz, 1H), 6.83 (d, J=8.0 Hz, 1H). MS (ESI) m/z: 304 (M+H)+.

Sources & evidence

ORD record: ord-2a896a182dd24f608fb07ae64d8f652d
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855205B2

Reaction notes

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