Iodine → HCID 15294637, compound

HRID 35899Notes

Reaction equation

HRID 35899 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:21])[CH:12]=[C:13]([SH:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.II.C(N(CC)CC)C>C(Cl)Cl>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[C:11](=[O:21])[CH:12]=[C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:20]1

Participants

5

Reactant 3

HCID 807IodineHCID 8471TriethylamineHCID 86748655N-(2-benzothiazolyl)-3-mercapto-3-phenylpropenamide

Product 1

HCID 15294637HCID 15294637, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 0.250 g (0.800 mmol) N-(2-benzothiazolyl)-3-mercapto-3-phenylpropenamide and 10 mL methylene chloride was stirred at room temperature. Added was 0.203 g (0.800 mmol) iodine dissolved in 10 mL methylene chloride and the mixture stirred 5 mins. Added next was 0.5 mL (excess) triethylamine and the mixture stirred for one hour. Solvent was evaporated and the residue dissolved in ethyl acetate and washed with water. The organic layer was dried, filtered and solvent was evaporated. The resulting solid was recrystallized from absolute ethanol to provide 0.090 g (0.290 mmol, 36%) N-(2-benzothiazolyl)-5-phenyl-4-isothiazolin-3-one as a very pale, yellow solid, mp=201°-202° C. NMR (CDCl3 /TMS): 6.6 (s, 1H)7.3-7.95 (m, 9H). IR (Nujol): 1680. High resolution mass spectrum: Calculated; 311.031282. Measured; 311.030775. Anal. calcd. for C16H10N2OS2 : C 61.91, H 3.25, N 9.03, S 20.66; Found C 61.82, H 3.14, N 8.97, S 20.55.

Workup

  1. additionAdded
  2. stirringthe mixture stirred 5 mins
  3. additionAdded next
  4. stirringthe mixture stirred for one hour
  5. customSolvent was evaporated
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water
  8. customThe organic layer was dried
  9. filtrationfiltered
  10. customsolvent was evaporated
  11. customThe resulting solid was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-e640c352e245456b8a8c6d72153d204f
Source dataset
uspto-grants-1995_05
Patent number
US05411977

Reaction notes

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