Water → HCID 585597, compound

HRID 972644Notes

Reaction equation

HRID 972644 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C(OCC)C.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>C(OCC)(=O)C>[C:20]1([NH:19][C:11]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)=[O:12])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6115AnilineHCID 989151-Adamantanecarbonyl chloride

Product 1

HCID 585597HCID 585597, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dissolve 2.0 g. (10 mmoles) of 1-adamantane carboxylic acid chloride in 20 ml. of ethyl ether and add to 3.0 ml. (32.9 mmoles) of aniline. Stir the mixture 15 minutes, then add 20 ml. of water and 25 ml. of ethyl acetate. Separate the layers and extract the aqueous layer several times with ethyl acetate. Combine the extracts and wash with 2N hydrochloric acid, saturated sodium bicarbonate solution, and water. Dry the extract over anhydrous sodium sulfate, filter and evaporate to a residue. Crystallize the residue from ethyl acetate to obtain the product of this example, m.p. 196°-199° C.

Workup

  1. dissolutionDissolve 2.0 g
  2. additionadd 20 ml
  3. customSeparate the layers
  4. extractionextract the aqueous layer several times with ethyl acetate
  5. washwash with 2N hydrochloric acid, saturated sodium bicarbonate solution, and water
  6. customDry the
  7. extractionextract over anhydrous sodium sulfate
  8. filtrationfilter
  9. customevaporate to a residue
  10. customCrystallize the residue from ethyl acetate
  11. customto obtain the product of this example, m.p. 196°-199° C.

Sources & evidence

ORD record
ord-8a60ab3cfc144ed480d00f111210796b
Source dataset
uspto-grants-1977_10
Patent number
US04053509

Reaction notes

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