Water → HCID 54192608, compound

HRID 2231762Notes

Reaction equation

HRID 2231762 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6](C#N)[CH2:7][C:4]=2[CH:3]=1.C([N:14]([CH2:17]C)CC)C.C(O[C:23](=[O:25])[CH3:24])(=O)C.[OH2:26]>C(Cl)Cl.C1(C)C=CC=CC=1.C(O)C>[O:26]([CH:6]1[C:5]2[CH:10]=[CH:11][C:2]([NH:1][C:23](=[O:25])[CH3:24])=[CH:3][C:4]=2[CH2:7]1)[C:17]#[N:14]

Participants

8

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13560713HCID 13560713, compound

Product 1

HCID 54192608HCID 54192608, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent3×

Procedure

About 4 g (0.02 moles) of 4-amino-1-cyanobenzocyclobutane is placed in a 100 ml flask equipped with an addition funnel, thermometer and nitrogen inlet. Additionally, 3.3 g (0.03 moles) of triethylamine in 60 ml of methylene chloride is added. A solution of acetic anhydride, 3.4 g (0.03 moles) in 5 ml of methylene chloride is added dropwise while keeping the temperature at below 5° C. Once addition is completed, the reaction is allowed to warm to room temperature overnight. The reaction mixture is added to 400 ml of water and stirred with magnetic stirrer and 50 ml of methylene chloride is added to dissolve the gummy solid. The methylene chloride layer is extracted and washed with 200 ml saturated sodium carbonate, 200 ml of water, 200 ml of 10 percent hydrochloric acid and then washed twice with 300 ml of water. The solution is dried over magnesium sulfate, filtered and the solvent is evaporated to yield an off-white solid. The solid is dissolved in a 70:30 volume percent mixture of toluene and ethanol and the product is recrystallized and recovered. The monomer has a melting point of between 163° and 168° C.

Workup

  1. customequipped with an addition funnel
  2. customat below 5° C
  3. additionOnce addition
  4. dissolutionto dissolve the gummy solid
  5. extractionThe methylene chloride layer is extracted
  6. washwashed with 200 ml saturated sodium carbonate, 200 ml of water, 200 ml of 10 percent hydrochloric acid
  7. washwashed twice with 300 ml of water
  8. dry with materialThe solution is dried over magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent is evaporated
  11. customto yield an off-white solid
  12. customthe product is recrystallized
  13. customrecovered

Sources & evidence

ORD record
ord-ca1c6dc97312499794d3e4d9c211e534
Source dataset
uspto-grants-1988_11
Patent number
US04783514

Reaction notes

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