4-Aminobenzyl alcohol → HCID 11574576, compound

HRID 729298Notes

Reaction equation

[CH2:1]([N:5]1[C:9](=[O:10])[C:8](Cl)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].[NH2:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=1>CN(C=O)C>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH2:27][OH:28])=[CH:23][CH:22]=2)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 140 °C

Procedure

2-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxide (110 mg, 0.331 mmol) was dissolved in dry DMF (0.5 mL) under nitrogen atmosphere. (4-Aminophenyl)methanol (122 mg, 0.991 mmol) was added and the reaction mixture was heated in a microwave reactor for 25 mins at 140° C. The crude product was purified by preparative HPLC affording the title compound (6 mg, 4.7%). 1H NMR (500 MHz, CD3CN): δ 1.00 (t, 3H), 1.43-1.52 (m, 2H), 1.78-1.85 (m, 2H), 3.03 (t, 1H), 3.75 (t, 2H), 4.40 (d, 2H), 6.77 (d, 2H), 6.97 (d, 2H), 7.13-7.19 (m, 4H), 7.24-7.28 (m, 1H), 7.76 (bs, 1H).

Workup

customThe crude product was purified by preparative HPLC

Sources & evidence

ORD record: ord-d23091d828e04d1bb5524b62a8abd441
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07582629B2

Reaction notes

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