Methylamine → 17681-30-0

HRID 1601058Notes

Reaction equation

HRID 1601058 reaction equation
Br[CH2:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][NH2:13]>C1COCC1>[CH3:12][NH:13][CH2:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 27762582-(Bromomethyl)-1,3-benzothiazole

Product 1

HCID 496262617681-30-0Yield 115.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromomethylbenzothiazole (0.4 g. 1.75 mmol) in THF (4 mL) was added 40% aqueous methylamine (0.30 g, 8.77 mmol). Stirring was continued overnight, then the mixture was concentrated. The residue was taken up in H2O, neutralized with 2.5 N NaOH, and extracted with CH2Cl2. The organic extracts were dried (MgSO4) and concentrated to give the title compound (0.36 g, 80%) as a brown oil: 1H NMR (250 MHz, DMSO-d6): δ 2.70 (s, 3H), 4.71 (s, 2H), 7.55 (m, 2H), 8.0 (d, J=7.9 Hz, 1H), 8.17 (d, J=7.9 Hz, 1H).

Workup

  1. concentrationthe mixture was concentrated
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic extracts were dried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a1c291cc371e4df988c240cc99d73534
Source dataset
uspto-grants-1999_11
Patent number
US05977101

Reaction notes

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