Chloroacetyl chloride → HCID 66781769, compound

HRID 1095316Notes

Reaction equation

HRID 1095316 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 60 F). Rf=0.23 (ethyl acetate-heptane 2:1), Rt=2.88 (gradient I).

Workup

  1. customThe mixture is evaporated

Sources & evidence

ORD record
ord-891992ec1d5a4c69a5302c5de2a80254
Source dataset
uspto-grants-2012_03
Patent number
US08138176B2

Reaction notes

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