Acetyl chloride → HCID 21245915, compound

HRID 620220Notes

Reaction equation

HRID 620220 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][NH:8][C:9]([O:11][CH2:12][C:13]1([CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:17][CH2:16][CH2:15][O:14]1)=[O:10].[C:38](Cl)(=[O:40])[CH3:39].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:38]([N:8]([CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:9]([O:11][CH2:12][C:13]1([CH2:18][O:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37])[CH2:17][CH2:16][CH2:15][O:14]1)=[O:10])(=[O:40])[CH3:39]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 21245903HCID 21245903, compound

Product 1

HCID 21245915HCID 21245915, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 0.259 g (0.5 mmol) of the compound prepared in (b) above dissolved in 3 ml of chloroform was added, with stirring and under a nitrogen atmosphere, 0.393 g (5.0 mmol) of acetyl chloride. The resultant mixture was cooled in an ice bath and to the cooled mixture was added, dropwise, 0.51 g (5.0 mmol) of triethylamine. The resultant solution was then warmed to reflux and maintained at the reflux temperature for 2 hours. The volatiles were then removed under high vacuum and the resultant residue was dissolved in methylene chloride and washed rapidly with a saturated aqueous sodium bicarbonate solution. The organic layer was then dried over sodium sulfate, filtered and concentrated. The resultant residue was then chromatographed on silica gel employing, successively as the eluents, a mixture of petroleum ether and ethyl acetate in a ratio of 4:1 by volume initially, with the product being eluted when the eluent was at a ratio of 7:3 by volume. The resultant solution was then concentrated to yield an oil.

Workup

  1. additionwas added
  2. additionwas added
  3. temperatureto reflux
  4. temperaturemaintained at the reflux temperature for 2 hours
  5. customThe volatiles were then removed under high vacuum
  6. dissolutionthe resultant residue was dissolved in methylene chloride
  7. washwashed rapidly with a saturated aqueous sodium bicarbonate solution
  8. dry with materialThe organic layer was then dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resultant residue was then chromatographed on silica gel employing, successively as the eluents
  12. additiona mixture of petroleum ether and ethyl acetate in a ratio of 4:1 by volume initially
  13. washwith the product being eluted when the eluent
  14. concentrationThe resultant solution was then concentrated
  15. customto yield an oil

Sources & evidence

ORD record
ord-95c5d4d071d94726ad6a7a24709d52c2
Source dataset
uspto-grants-1989_04
Patent number
US04820718

Reaction notes

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