Chloroacetyl chloride → 2-(2-Chloroacetylamino)-1,1-diphenylethanol

HRID 974203Notes

Reaction equation

HRID 974203 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH2:6][CH:7](C)[C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9].C(N(CC)CC)C>C1COCC1>[Cl:1][CH2:2][C:3]([NH:6][CH2:7][C:8]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[OH:9])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2341582-Amino-1,1-diphenylpropan-1-ol

Product 1

HCID 199855732-(2-Chloroacetylamino)-1,1-diphenylethanolYield 85.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 0.33 ml (0.975 g, 4.2 mmol) chloroacetyl chloride in 10 ml THF was cooled to 0° C. To this was added a solution of 0.8 g (3.98 mmol) 2-amino-1,1-diphenylpropanol and 0.6 ml (0.436 g, 4.31 mmol) triethylamine in 10 ml THF. The resulting solution was stirred at 0° C. for 2 hours before it was filtered and the residue washed with THF. The combined filtrate was concentration and the residue crystallized from ethyl acetate-hexane to afford 0.986 g (78%) of 2-(2-chloroacetylamino)-1,1-diphenylethanol, m.p. 178°-180° C.

Workup

  1. filtrationwas filtered
  2. washthe residue washed with THF
  3. concentrationconcentration
  4. customthe residue crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0a8ecb587b2640238417e100709f5fe5
Source dataset
uspto-grants-1991_11
Patent number
US05068248

Reaction notes

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