Triethylamine → HCID 53883590, compound

HRID 486068Notes

Reaction equation

HRID 486068 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:11][N:10]=[C:9]([CH:12]2[CH2:14][CH2:13]2)[N:8]=1.[C:15](Cl)(Cl)=[S:16].Cl.Cl.N[CH:22]1[CH:27]2[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]2)[CH2:23]1.[OH-].[Na+].C(=O)(O)[O-].[Na+].C([N:39](CC)CC)C>C(Cl)Cl.O>[CH:12]1([C:9]2[N:8]=[C:7]([C:3]3[S:4][CH:5]=[CH:6][C:2]=3[N:1]([CH:22]3[CH:27]4[CH2:28][CH2:29][N:24]([CH2:25][CH2:26]4)[CH2:23]3)[C:15]([NH2:39])=[S:16])[O:11][N:10]=2)[CH2:14][CH2:13]1

Participants

9

Reactant 6

HCID 8471TriethylamineHCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 197853Quinuclidine, 3-amino-, dihydrochlorideHCID 516892Sodium BicarbonateHCID 19097461HCID 19097461, compound

Product 1

HCID 53883590HCID 53883590, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

3-Amino-2-(3-cyclopropyl-1,2,4-oxadiazol-5-yl)thiophene (1.0 g, 5 mmol) in 10 ml dry methylene chloride was added dropwise to a vigorously stirred mixture of thiophosgene (10.5 ml, 6.5 mmol) in 10 ml H2O. Upon addition 1.0 ml triethylamine was added and stirring continued for 20 min. whereupon the organic phase was isolated and the aqueous phase was washed with methylene chloride. The combined organic phases were added to a solution of 3-aminoquinuclidine, dihydrochloride (1.2 g, 6 mmol) dissolved in 1 ml H2O and made alkaline with 50% NaOH. This mixture was then stirred at room temperature for 6 hours whereupon 5 ml saturated sodium bicarbonat was added. The desired product was isolated by filtration, washed with water and dried to give 0.2 g. M.p. 155°-157° C.

Workup

  1. additionwas added
  2. customwas isolated
  3. washthe aqueous phase was washed with methylene chloride
  4. additionwas added

Sources & evidence

ORD record
ord-1a63664473944fe9a9ca75e85697f22a
Source dataset
uspto-grants-1994_03
Patent number
US05290795

Reaction notes

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