Chloroacetyl chloride → HCID 68908542, compound

HRID 1191489Notes

Reaction equation

[CH2:1]([C:3]1[C:8]([OH:9])=[C:7]([NH2:10])[CH:6]=[CH:5][CH:4]=1)[CH3:2].Cl[CH2:12][C:13](Cl)=[O:14].C([O-])([O-])=O.[K+].[K+]>>[CH2:1]([C:3]1[C:8]2[O:9][CH2:12][C:13](=[O:14])[NH:10][C:7]=2[CH:6]=[CH:5][CH:4]=1)[CH3:2]

Participants

Reactant 3

HCID 6577Chloroacetyl chloride

HCID 11430Potassium Carbonate

HCID 127914512-Amino-6-ethylphenol

Product 1

HCID 68908542HCID 68908542, compoundYield 61%

Procedure

6-Ethyl-2-aminophenol (0.88 g, 6.4 mmol), 2-chloroacetyl chloride (0.80 g, 7.0 mmol) and K2CO3 (1.86 g, 13.5 mmol) were mixed according to GP1. Purified by column chromatography (SiO2; CH2Cl2/MeOH 99:1) to give the title compound (0.69 g, 61%). Rf=0.54 (heptanes/EtOAc 1:1); 1H NMR (CDCl3) δ 9.29 (s, 1H), 6.92-6.85 (m, 2H), 6.71 (dd, J=7.0 Hz, J=2.6 Hz), 4.62 (s, 2H), 2.65 (q, J=7.6 Hz, 2H), 1.20 (t, J=7.6 Hz, 3H); 13C NMR (CDCl3) δ 166.8, 141.6, 133.0, 126.1, 124.4, 122.5, 114.0, 67.3, 22.9, 14.4.

Workup

customPurified by column chromatography (SiO2; CH2Cl2/MeOH 99:1)

Sources & evidence

ORD record: ord-fe940ce038314d1fbcfe2d43f7fb474c
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680115B2

Reaction notes

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