Phosgene → HCID 23169337, compound

HRID 1729033Notes

Reaction equation

HRID 1729033 reaction equation
[C:1](Cl)(Cl)=[O:2].[NH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[O:16][N:15]=[C:14]([CH:17]2[CH2:19][CH2:18]2)[N:13]=1.C([N:22](CC)CC)C.N[CH:28]1[CH:33]2[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]2)[CH2:29]1>C1(C)C=CC=CC=1.C(Cl)Cl>[CH:17]1([C:14]2[N:13]=[C:12]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=3[N:5]([CH:28]3[CH:33]4[CH2:34][CH2:35][N:30]([CH2:31][CH2:32]4)[CH2:29]3)[C:1]([NH2:22])=[O:2])[O:16][N:15]=2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 1232383-AminoquinuclidineHCID 19013331HCID 19013331, compound

Product 1

HCID 23169337HCID 23169337, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of phosgene in toluene (1.5 ml, 1.9M) stirred under N2 at 0° C. was added dropwise 5-(2-aminophenyl)-3-cyclopropyl-1,2,4-oxadiazol (0.5 g, 2.5 mmol) in 30 mldry methylene chloride and then 0.8 ml of dry triethylamine. Upon addition the mixture was stirred at 0° C. for 15 min. whereupon a solution of 3-aminoquinuclidine (0.18 g, 1.4 mmol) in 10 ml CH2Cl2 was added. This mixture was stirred at room temperature for 4 h and washed with 25 ml saturated sodium bicarbonate. The organic phase was dried with magnesium sulphate and concentrated in vacuo. The resulting oil dissolved in methanol. Addition of ether precipitated 0.38 g of the desired product as white crystals. This product was dissolved in ethanol and precipitated as the hydrochloride by addition of dry hydrochloric acid in ether, giving0.3 g. M.p. 229°-233° C.

Workup

  1. additionUpon addition the mixture
  2. additionwas added
  3. washwashed with 25 ml saturated sodium bicarbonate
  4. dry with materialThe organic phase was dried with magnesium sulphate
  5. concentrationconcentrated in vacuo
  6. dissolutionThe resulting oil dissolved in methanol
  7. additionAddition of ether
  8. customprecipitated 0.38 g of the desired product as white crystals
  9. dissolutionThis product was dissolved in ethanol
  10. customprecipitated as the hydrochloride by addition of dry hydrochloric acid in ether, giving0

Sources & evidence

ORD record
ord-a561e12a5b424ea18ac4d95819496ca7
Source dataset
uspto-grants-1994_07
Patent number
US05330990

Reaction notes

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