Sodium Iodide → HCID 54296994, compound

HRID 1904148Notes

Reaction equation

HRID 1904148 reaction equation
Br[CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8].[I-:37].[Na+]>C(C(C)=O)C>[I:37][CH2:2][CH2:3][O:4][N:5]=[C:6]([C:12]1[N:13]=[C:14]([NH:17][C:18]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:15][CH:16]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 53679114Ethyl 2-(bromoethoxyimino)-2-(2-tritylamino-4-thiazolyl)-acetate

Product 1

HCID 54296994HCID 54296994, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 6 g of the syn isomer of ethyl 2-(2-bromoethoxyimino)-2-(2-tritylamino-4-thiazolyl)-acetate, 60 ml of methyl ethyl ketone and 2.141 g of sodium iodide was refluxed for 70 minutes and was then evaporated to dryness under reduced pressure. The residue was taken up in 120 ml of methylene chloride and the solution was washed 5 times with 40 ml of water. Each of the wash waters were reextracted with 2 ml of methylene chloride and the combined organic phase were dried and evaporated to dryness. The resin residue was added to ether and the solution was evaporated to dryness under reduced pressure to obtain 6.22 g of the syn isomer of ethyl 2-(2-iodoethoxyimino)-2-(2-tritylamino-4-thiazolyl)acetate melting at 110° C.

Workup

  1. temperaturewas refluxed for 70 minutes
  2. customwas then evaporated to dryness under reduced pressure
  3. washthe solution was washed 5 times with 40 ml of water
  4. customthe combined organic phase were dried
  5. customevaporated to dryness
  6. additionThe resin residue was added to ether
  7. customthe solution was evaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-5cf8791f3126413d8f4e68d23f7cdfaf
Source dataset
uspto-grants-1984_03
Patent number
US04439433

Reaction notes

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