Chloroacetyl chloride → 2-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamide

HRID 1365088Notes

Reaction equation

HRID 1365088 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3.C(N(CC)CC)C.[Cl:23][CH2:24][C:25](Cl)=[O:26]>ClCCl>[Cl:23][CH2:24][C:25]([NH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:15])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][CH:10]=[CH:9][CH:8]=3)=[O:26]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 2352713-Amino-9-fluorenone

Product 1

HCID 114486452-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-amino-9-fluorenone (1.95 g, 10 mmols), triethylamine (2.07 ml, 15 mmols), in 25 ml of dried dichloromethane, is cooled to 10° C. and a solution of chloroacetyl chloride (1.18 g, 10.5 mmoles) in 10 ml of dried dichloromethane is then added drop by drop. The resulting mixture is kept stirring for 1 hour at room temperature overnight. The mixture is washed with 2×30 ml of water, dried over sodium sulfate and evaporated. 2.63 g 2-Chloro-N-(9-oxo-9H-fluoren-3-yl)-acetamide (97%) are obtained.

Workup

  1. washThe mixture is washed with 2×30 ml of water
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-8e3a9ac3000043698ebe8c14214d1269
Source dataset
uspto-grants-2011_02
Patent number
US07888510B2

Reaction notes

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