Sodium Iodide → HCID 68818863, compound

HRID 1819740Notes

Reaction equation

HRID 1819740 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.[CH2:11]([Cl:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[I-].[Na+]>COC(O)C>[ClH:18].[CH2:11]([N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]1=[NH:1])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 7503Benzyl ChlorideHCID 8706Benzo(d)thiazol-2-amine

Product 1

HCID 68818863HCID 68818863, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 30156371-MethoxyethanolSolvent

Procedure

A mixture of 2-aminobenzothiazole (2.116 g, 13.7 mmol), benzyl chloride (2.1 mL, 18.2 mmol) and sodium iodide (200 mg) were refluxed for 8 hours in methoxyethanol (25 mL). Crystallization occurred upon cooling. The crystals were filtered off and thoroughly washed with ether to give yellow crystals in 39% yield: mp 275-278° C.; 1H-NMR (DMSO-d6) 5.65 (s, 2H), 7.28, (d, 2H), 7.36 (m, 4H), 7.50 (t, 1H), 7.55 (d, 1H) 8.02 (s, 1H); HR-MS (EI) m/z 240.0719 (M+).

Workup

  1. customCrystallization
  2. temperatureupon cooling
  3. filtrationThe crystals were filtered off
  4. washthoroughly washed with ether
  5. customto give yellow crystals in 39% yield

Sources & evidence

ORD record
ord-ebf2bd19bef74089ac343c76ef21322d
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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