Acetyl chloride → HCID 70351280, compound

HRID 978467Notes

Reaction equation

HRID 978467 reaction equation
[CH3:1][C:2]([N:5]1[CH2:9][CH:8]([CH2:10][O:11][C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][OH:20])=[CH:14][CH:13]=2)[O:7][C@H:6]1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([CH3:4])[CH3:3].[C:27](Cl)(=[O:29])[CH3:28]>N1C=CC=CC=1>[C:27]([O:20][CH2:19][CH2:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][CH2:10][CH:8]2[O:7][C@@H:6]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[CH2:9]2)=[CH:13][CH:14]=1)(=[O:29])[CH3:28]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 54082836HCID 54082836, compound

Product 1

HCID 70351280HCID 70351280, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-15 °C

Procedure

The residue from Example 1, Step A (2.55 g, 6.3 mmol) was dissolved in pyridine (10 ml), cooled to -15° C. and acetyl chloride (547 mg, 6.9 mmol) was added. The mixture was stirred at 0° C. for 3 hours then at room temperature overnight. The solvent was removed in vacuo. To the residue, dil. Na2CO3 solution was added (30 ml) and the mixture was extracted with CHCl3 (50 ml then 20 ml). The combined CHCl3 extracts were washed with H2O (30 ml), dried over Na2SO4 and evaporated in vacuo. The residue was used directly in the next step without further purification.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solvent was removed in vacuo
  4. additionTo the residue, dil. Na2CO3 solution was added (30 ml)
  5. extractionthe mixture was extracted with CHCl3 (50 ml
  6. washThe combined CHCl3 extracts were washed with H2O (30 ml)
  7. dry with materialdried over Na2SO4
  8. customevaporated in vacuo
  9. customThe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-c55ca50272ee42efaea480f484eb10e6
Source dataset
uspto-grants-1987_05
Patent number
US04665094

Reaction notes

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