Methyl iodide → 2-(Methylthio)benzo[d]thiazol-6-ol

HRID 2370511Notes

Reaction equation

HRID 2370511 reaction equation
[SH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:12](N(CC)CC)C.IC>C(Cl)Cl>[CH3:12][S:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([OH:11])[CH:8]=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 8471TriethylamineHCID 178515779HCID 178515779, compound

Product 1

HCID 450774142-(Methylthio)benzo[d]thiazol-6-olYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the ice cooled solution of 2-mercapto-benzothiazol-6-ol from step 1 (3.80 g, 20.76 mmol, 1.0 eq) in DCM (40 mL, 0.5M) at 0° C., was added triethylamine (7.29 mL, 51.91 mmol, 2.5 eq) followed by iodomethane (1.93 mL, 31.14 mmol, 1.5 eq). The reaction was stirred from 0° C. to −10° C. for 3 hours. The solvent was removed in vacuo. Water (ca. 200 mL) was added and the aqueous layer was extracted with ethyl acetate (3×150 mL). The organic layer was dried over sodium sulfate, filtered, and evaporated in vacuo to yield 2-methylsulfanyl-benzothiazol-6-ol as light green powder (3.76 g, 92%). The crude product was used in the next step without purification. M+H=198.0

Workup

  1. customThe solvent was removed in vacuo
  2. additionWater (ca. 200 mL) was added
  3. extractionthe aqueous layer was extracted with ethyl acetate (3×150 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-707dcd1001b74e1fa7880c82bdf8a157
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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