Chloroacetyl chloride → HCID 20150679, compound

HRID 1733317Notes

Reaction equation

HRID 1733317 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH3:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[NH:17][CH:18]1[CH2:23][O:22][C:20](=[O:21])[CH2:19]1>C1(C)C=CC=CC=1>[Cl:1][CH2:2][C:3]([N:17]([CH:18]1[CH2:23][O:22][C:20](=[O:21])[CH2:19]1)[C:8]1[C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:15]=[CH:16][C:7]=1[CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 13191334HCID 13191334, compound

Product 1

HCID 20150679HCID 20150679, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 2.4-g (0.020 mol) sample of chloroacetyl chloride was added to a refluxing solution of 5.0 g (0.021 mol) 3-(N-2-methylnaphth-1-ylamino)-gamma-butyrolactone in 100 ml toluene. The reaction mixture was heated under reflux for 30 minutes. Gas was evolved and a white precipitate formed during the 30-minute reflux period. The reaction mixture was cooled, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give 4.3 g of product, as a white solid, m.p. 121°-122° C. The infrared spectrum of the product showed two strong carbonyl absorption bands at 5.62 microns and 5.88 microns. The product is tabulated in Table C as Compound No. C-1.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 30 minutes
  3. customa white precipitate formed during the 30-minute
  4. temperaturereflux period
  5. temperatureThe reaction mixture was cooled
  6. washwashed with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-967d4291ca584769a0ffb09444f4a952
Source dataset
uspto-grants-1980_12
Patent number
US04241078

Reaction notes

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