Chloroacetyl chloride → HCID 66781769, compound

HRID 1360151Notes

Reaction equation

HRID 1360151 reaction equation
[NH2:1][C:2]([C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1)([CH3:5])[CH2:3][OH:4].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(#N)C.CO>[Cl:21][CH2:22][C:23]([NH:1][C:2]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)([CH3:5])[CH2:3][OH:4])=[O:24]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 61054422HCID 61054422, compound

Product 1

HCID 66781769HCID 66781769, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 57.5 mmol of 2-amino-2-(4-methoxyphenyl)propan-1-ol in 190 ml of acetonitrile and 33 ml of methanol is cooled to −10° C., and 69 mmol of triethylamine and, dropwise over the course of 1 hour, 63.3 mmol of chloroacetyl chloride are successively added. The reaction mixture is warmed to room temperature and stirred for 16 hours. The mixture is evaporated, and the title compound is obtained as a colourless oil from the residue by flash chromatography (SiO2 60F). Rf=0.23 (ethyl acetate-heptane 2:1), Rt=2.88 (gradient I).

Workup

  1. customThe mixture is evaporated

Sources & evidence

ORD record
ord-e23367976ff94b11a5f1beb46feef9ff
Source dataset
uspto-grants-2011_02
Patent number
US07879847B2

Reaction notes

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