Sodium Iodide → HCID 11652215, compound

HRID 1819741Notes

Reaction equation

HRID 1819741 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][Cl:17])=[CH:14][CH:13]=1.[I-].[Na+]>COC(O)C>[ClH:17].[CH3:11][C:12]1[CH:19]=[CH:18][C:15]([CH2:16][N:6]2[C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[S:3][C:2]2=[NH:1])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 77224-Methylbenzyl chlorideHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 11652215HCID 11652215, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

A mixture of 2-aminobenzothiazole (2.104 g, 13.6 mmol) and 4-methylbenzyl chloride (2.25 mL, 12.5 mmol) was refluxed for 8 hours in methoxyethanol in the presence of a catalytic amount of sodium iodide (220 mg, 1.46 mmol). After cooling a precipitate formed which was filtered and rinsed with ether to give 35% yield: mp 243-248° C.; 1H-NMR (DMSO-d6) 2.26 (s, 3H), 5.65 (s, 2H), 7.20 (dd, 4H), 7.39 (t, 1H), 7.48 (t, 1H), 7.55 (d, 1H), 8.02 (d, 1H); HR-MS (EI) m/z 254.0870 (M+).

Workup

  1. temperatureAfter cooling a precipitate
  2. customformed which
  3. filtrationwas filtered
  4. washrinsed with ether
  5. customto give 35% yield

Sources & evidence

ORD record
ord-81a5a80446da4815b046eeb0ed36eb8e
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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