Methanol → HCID 56632022, compound

HRID 485047Notes

Reaction equation

HRID 485047 reaction equation
[CH3:1][N:2]([CH2:10][C:11]#[C:12][I:13])[C:3]1[S:4][CH:5]=[C:6]([CH:8]=O)[N:7]=1.CO.Cl.[NH2:17][OH:18]>C(N(CC)CC)C>[CH3:1][N:2]([CH2:10][C:11]#[C:12][I:13])[C:3]1[S:4][CH:5]=[C:6]([CH:8]=[N:17][OH:18])[N:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 13344834HCID 13344834, compound

Product 1

HCID 56632022HCID 56632022, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 2-(N-methyl-3-iodo-2-propynylamino)-4-formylthiazole (No. 21) (72 mg) were added methanol (5 ml), triethylamine (0.2 ml) and hydroxylamine hydrochloride (24 mg) and the mixture was stirred at room temperature for 4 hours and evaporated to remove the solvent. After addition of a 5% aqueous solution of potassium carbonate, the residue was extracted with chloroform. The extract was washed with water, dried and evaporated to remove the solvent. The crystalline residue was treated with acetone to give 2-(N-methyl-3-iodo-2-propynylamino)-4-hydroxyiminomethylthiazole (No. 22) melting at 155°-156° C. (decomp.).

Workup

  1. customevaporated
  2. customto remove the solvent
  3. additionAfter addition of a 5% aqueous solution of potassium carbonate
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with water
  6. customdried
  7. customevaporated
  8. customto remove the solvent
  9. additionThe crystalline residue was treated with acetone

Sources & evidence

ORD record
ord-c07c5450d34f48089eb690e8f660bed0
Source dataset
uspto-grants-1985_08
Patent number
US04535088

Reaction notes

Loading…