Iodoacetamide → HCID 20475727, compound

HRID 905218Notes

Reaction equation

HRID 905218 reaction equation
Cl.[CH3:2][C:3]1[C:8]([Br:9])=[C:7]([CH3:10])[NH:6][C:5](=[S:11])[N:4]=1.[OH-].[K+].I[CH2:15][C:16]([NH2:18])=[O:17]>>[C:16]([CH2:15][S:11][C:5]1[N:6]=[C:7]([CH3:10])[C:8]([Br:9])=[C:3]([CH3:2])[N:4]=1)(=[O:17])[NH2:18]

Participants

4

Reactant 3

HCID 3727IodoacetamideHCID 14797Potassium HydroxideHCID 20475758HCID 20475758, compound

Product 1

HCID 20475727HCID 20475727, compoundYield 72%

Procedure

4,6-Dimethyl-5-bromopyrimidine-2-thione HCl salt (5 mmol) was added to ethanolic (60 ml) KOH (11.4 mmol), the solution stirred for 10 min at room temperature, iodoacetamide (5.7 mmol) added, the stirring continued for 20 min at room temperature and for 100 min at 70° C. (pH 8). The warm reaction mixture was filtered, the filtrate evaporated, the residue extracted with chloroform (150 ml), the chloroform solution washed and the dried (MgSO4) solution evaporated to leave the sulfide; yield 72%, m.p. 175°-177° C. (iPrOH). 1H NMR (DMSO-d6): δ2.50 (Me), 3.80 (SCH2).

Workup

  1. waitthe stirring continued for 20 min at room temperature and for 100 min at 70° C.
  2. customThe warm reaction mixture
  3. filtrationwas filtered
  4. customthe filtrate evaporated
  5. extractionthe residue extracted with chloroform (150 ml)
  6. washthe chloroform solution washed
  7. dry with materialthe dried (MgSO4) solution
  8. customevaporated

Sources & evidence

ORD record
ord-f8ddfa65af6b4e8a8b3021742794d2bf
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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