Diisopropylethylamine → Pyridine-2-sulfonic acid 4-hydroxymethyl-benzylamide

HRID 2308301Notes

Reaction equation

HRID 2308301 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][OH:10])=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27]>>[OH:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([CH2:2][NH:1][S:26]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)(=[O:28])=[O:27])=[CH:4][CH:5]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 3787675Pyridine-2-sulfonyl ChlorideHCID 6496943[4-(Aminomethyl)phenyl]methanol

Product 1

HCID 68898056Pyridine-2-sulfonic acid 4-hydroxymethyl-benzylamideYield 85%

Procedure

Using the above procedure J: Reaction of (4-aminomethyl-phenyl)-methanol (255 mg, 1.86 mmol, N,N-diisopropylethylamine (294 μL, 1.69 mmol), and pyridine-2-sulfonyl chloride (300 mg, 1.69 mmol) for 10 minutes at room temperature gave the title compound (400 mg, 85%) white solid. 1H NMR (300 MHz, CDCl3) δ 4.26 (br s, 2H), 4.66 (br s, 2H), 5.28 (br s, 1H), 7.23-7.30 (m, 4H), 7.49-7.51 (m, 1H), 7.90-7.92 (m, 1H), 7.99 (d, 1H, J=4.8 Hz), 8.68 (d, 1H, J=4.5 Hz).

Sources & evidence

ORD record
ord-8b81e99de81d4417b4d1b92b6cef9c44
Source dataset
uspto-grants-2004_12
Patent number
US06835731B2

Reaction notes

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