Chloroacetyl chloride → HCID 15524338, compound

HRID 1976694Notes

Reaction equation

HRID 1976694 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.C(N(CC)CC)C.[Cl:18][CH2:19][C:20](Cl)=[O:21]>C(Cl)Cl>[Cl:18][CH2:19][C:20]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)=[O:21]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 5834314-Aminoindole

Product 1

HCID 15524338HCID 15524338, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-aminoindole (1.0 g, 7.57 mmol), triethylamine (1.07 mL, 7.57 mmol) in methylene chloride (50 mL) at 0° C., was added dropwise a solution of chloroacetyl chloride (0.615 mL, 7.57 mmol) in methylene chloride (5 mL). After 30 minutes, the solution was washed with water (2×100 mL) and dried over anhydrous magnesium sulfate. Purification by chromatography over silica gel (60 g, 40% ethyl acetate-hexane) and crystallization form hexane-ethyl acetate afforded the title compound as a white solid (1.17 g, 74.1%), mp 114-116° C.; MS EI m/e 208/210 (M+).

Workup

  1. washthe solution was washed with water (2×100 mL)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customPurification by chromatography
  4. customover silica gel (60 g, 40% ethyl acetate-hexane) and crystallization
  5. customform hexane-ethyl acetate

Sources & evidence

ORD record
ord-e29e1af6564d4a6b884a4219200dd0e5
Source dataset
uspto-grants-2001_05
Patent number
US06228880B1

Reaction notes

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