Acetone → HCID 19788972, compound

HRID 1655810Notes

Reaction equation

HRID 1655810 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](C(O)=O)=[C:2]1[C:9]1[S:10][CH:11]=[CH:12][CH:13]=1.S(Cl)(Cl)=O.[C:18](Cl)(Cl)=[O:19].[N-]=[N+]=[N-].[N-:25]=[N+]=[N-].[Na+].[CH3:29][C:30](C)=[O:31]>O.C(O)C>[CH2:30]([O:31][C:18]([NH:25][C:11]1[S:10][C:9]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)=[CH:13][CH:12]=1)=[O:19])[CH3:29]

Participants

9

Reactant 6

HCID 180AcetoneHCID 6371Phosgene2×HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 33558AzideHCID 19788982HCID 19788982, compound

Product 1

HCID 19788972HCID 19788972, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Bithienylcarboxylic acid in a quantity of 12.3 g is refluxed with 25 ml thionylchloride for 30 min. After evaporating in vacuo the residual carbonylchloride is obtained in a yield of 13.7 g; m.p. 74° C. The carbonylchloride is converted to the corresponding azide by adding a solution of 1.6 g sodium azide in 5 ml water to a solution of said carbonylchloride in 25 ml of acetone. After 30 min at 0° C., ice water is added and the solid is sucked off. After drying 5-azido-carbonyl-2,2'-bithiophene is obtained in a yield of 4.6 g; m.p. 76° C. A mixture of the azidocompound (4.6 g) and 50 ml of abs. ethanol is refluxed for approximately 8 h. After decoloration with charcoal, the filtrate is evaporated and the residue is crystallized from petroleum ether. The desired 5-ethoxycarbonylamino-2,2'-bithiophene is obtained in a yield of 2.4 g; m.p. 98° C. Elementary analysis: 52.45% C (calc. 52.15), 4.36% H (calc. 4.38), 5.63% N (calc. 5.53) and 25.73% S (calc. 25.32).

Workup

  1. customAfter evaporating in vacuo the residual carbonylchloride
  2. customis obtained in a yield of 13.7 g
  3. dry with materialAfter drying 5-azido-carbonyl-2,2'-bithiophene
  4. customis obtained in a yield of 4.6 g
  5. additionA mixture of the azidocompound (4.6 g) and 50 ml of abs
  6. customAfter decoloration with charcoal, the filtrate is evaporated
  7. customthe residue is crystallized from petroleum ether

Sources & evidence

ORD record
ord-09ae890543b54c358e82b24cf13a3b02
Source dataset
uspto-grants-1993_10
Patent number
US05252191

Reaction notes

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