Iodine → HCID 13344824, compound

HRID 485040Notes

Reaction equation

HRID 485040 reaction equation
[CH3:1][N:2]([CH2:9][C:10]#[CH:11])[C:3]1[S:4][C:5]([CH3:8])=[CH:6][N:7]=1.CCCCCC.C([Li])CCC.[I:23]I>O1CCCC1.C(Cl)(Cl)Cl>[CH3:1][N:2]([CH2:9][C:10]#[C:11][I:23])[C:3]1[S:4][C:5]([CH3:8])=[CH:6][N:7]=1

Participants

7

Reactant 4

HCID 807IodineHCID 8058HexaneHCID 13520360HCID 13520360, compoundHCID 178418339Butyllithium

Product 1

HCID 13344824HCID 13344824, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Procedure

Compound (b) (950 mg) was dissolved in anhydrous tetrahydrofuran (30 ml) and a hexane solution (4.5 ml) of butyllithium was added thereto at -78° C. After 30 minutes iodine (1.6 g) was added to the above mixture, which was then allowed to react for 10 minutes at room temperature and evaporated to remove the tetrahydrofuran. Water is added to the residue, which was then extracted with ether. The extract was washed with water and evaporated to remove the solvent. The residue was applied to chromatography on silica gel (25 g) to give 2-(N-methyl-3-iodo-2-propynylamino)-5-methylthiazole (No.1) (1.38 g, yield 83%) from chloroform eluate. mp. 97°-98° C. (hydrochloride: mp. 205°-213° C. (decomp.))

Workup

  1. customat -78° C
  2. customto react for 10 minutes at room temperature
  3. customevaporated
  4. customto remove the tetrahydrofuran
  5. additionWater is added to the residue, which
  6. extractionwas then extracted with ether
  7. washThe extract was washed with water
  8. customevaporated
  9. customto remove the solvent

Sources & evidence

ORD record
ord-50d4eea9721c43c09e1282474153fff5
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

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