Iodoethane → HCID 20252626, compound

HRID 638544Notes

Reaction equation

HRID 638544 reaction equation
[CH2:1](I)[CH3:2].[Cl:4][C:5]1[CH:6]=[C:7]([C:12]2([C:19]([NH2:21])=[O:20])[O:16][S:15](=[O:17])[NH:14][C:13]2=[O:18])[CH:8]=[CH:9][C:10]=1[Cl:11].C(N(CC)CC)C>C(#N)C>[CH2:1]([N:14]1[C:13](=[O:18])[C:12]([C:7]2[CH:8]=[CH:9][C:10]([Cl:11])=[C:5]([Cl:4])[CH:6]=2)([C:19]([NH2:21])=[O:20])[O:16][S:15]1=[O:17])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 8471TriethylamineHCID 20252638HCID 20252638, compound

Product 1

HCID 20252626HCID 20252626, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

31.2 g (0.2 mole) of ethyl iodide are added to a solution of 6.2 g (0.02 mole) of 5-(3,4-dichlorophenyl)-5-aminocarbonyl-1,2,3-oxathiazolidin-4-one-2-oxide and 2.02 g (0.02 mole) of triethylamine in 50 ml of acetonitrile. The solution is heated to the boil for four hours and then evaporated down under reduced pressure. The residue is taken up in 50 ml of dichloromethane, and the solution is washed with three times 20 ml of water. The organic phase is evaporated down and the residue is triturated with diethyl ether. In this manner, 4.7 g (70% of theory) of 3-ethyl-5-(3,4-dichlorophenyl)-5-aminocarbonyl-1,2,3-oxathiazolidin-4-one-2-oxide of melting point 127°-128° C. are obtained.

Workup

  1. temperatureThe solution is heated to the boil for four hours
  2. customevaporated down under reduced pressure
  3. washthe solution is washed with three times 20 ml of water
  4. customThe organic phase is evaporated down
  5. customthe residue is triturated with diethyl ether

Sources & evidence

ORD record
ord-c790519ebc7642cf9c251bcef4ea63d7
Source dataset
uspto-grants-1985_12
Patent number
US04562185

Reaction notes

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