Pivaloyl chloride → N-(2-Chloro-6-(hydroxymethyl)phenyl)pivalamide

HRID 132248Notes

Reaction equation

HRID 132248 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[CH3:11][C:12]([CH3:17])([CH3:16])[C:13](Cl)=[O:14].CCN(C(C)C)C(C)C>C(Cl)Cl>[Cl:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:9][OH:10])[C:2]=1[NH:1][C:13](=[O:14])[C:12]([CH3:17])([CH3:16])[CH3:11]

Participants

5

Reactant 3

HCID 62493Pivaloyl chlorideHCID 81531DiisopropylethylamineHCID 14155407(2-Amino-3-chlorophenyl)methanol

Product 1

HCID 67318310N-(2-Chloro-6-(hydroxymethyl)phenyl)pivalamideYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the crude (2-amino-3-chlorophenyl)methanol(1.08 g, 6.88 mmol) in CH2Cl2 (15 mL) was fast dropwise added trimethylacetyl chloride (0.89 mL, 7.23 mmol), followed by DIEA (2.4 mL, 13.8 mmol) at 0° C. 5 min later, the reaction mixture was stirred at room temperature for 1 hr. Normal aqueous work-up to afford the expected product as a white solid (1.58 g, 95% yield), which was pure enough to be used in next step; 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (s, 9 H), 3.35 (s, 2 H), 4.36 (d, J=6.29 Hz, 1 H), 7.06-7.22 (m, J=7.81, 7.81 Hz, 1 H), 7.29-7.33 (m, 2 H), 7.58 (s, 1 H); Mass spec. 242.08 (MH+), Calc. for C12H16ClNO2 241.09.

Sources & evidence

ORD record
ord-d73fdac8e83049aab9ec8a06ef64e34e
Source dataset
uspto-grants-2008_06
Patent number
US07384930B2

Reaction notes

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