Acetic Anhydride → HCID 12898838, compound

HRID 1659154Notes

Reaction equation

HRID 1659154 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([C:6]([NH:8][CH:9]2[CH2:13][CH2:12][N:11]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH2:10]2)=[O:7])=[CH:4][CH:3]=1.[C:22](OC(=O)C)(=[O:24])[CH3:23]>C(Cl)(Cl)Cl>[CH:14]1([N:11]2[CH2:12][CH2:13][CH:9]([NH:8][C:6](=[O:7])[C:5]3[CH:20]=[CH:21][C:2]([NH:1][C:22](=[O:24])[CH3:23])=[CH:3][CH:4]=3)[CH2:10]2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 234522034-Amino-N-(1-cyclohexylpyrrolidin-3-yl)benzamide

Product 1

HCID 12898838HCID 12898838, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 8.6 g. (0.3 mole) of p-amino-N-(1-cyclohexyl-3-pyrrolidinyl)benzamide in 50 ml. of chloroform was added dropwise with stirring, 3.37 g. (0.03 mole) of acetic anhydride. The mixture was stirred for 30 minutes and the solution extracted with dilute sodium hydroxide. The chloroform layer was dried over sodium sulfate, filtered and concentrated. The residue was dissolved in hot ethyl acetate and an equivalent amount of isopropyl ether added to precipitate the product. After recrystallizing from the same solvent, 5.1 g. (50%) of product melting at 184°-186°C. was obtained.

Workup

  1. additionTo a suspension of 8.6 g
  2. stirringThe mixture was stirred for 30 minutes
  3. extractionthe solution extracted with dilute sodium hydroxide
  4. dry with materialThe chloroform layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in hot ethyl acetate
  8. additionan equivalent amount of isopropyl ether added
  9. customto precipitate the product
  10. customAfter recrystallizing from the same solvent, 5.1 g

Sources & evidence

ORD record
ord-a5fa33e24bc74bc993a877b5c076b54f
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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