Benzo(d)thiazol-2-amine → 3-(3-Methoxy-propyl)-3H-benzothiazol-2-ylideneamine hydrobromide

HRID 1469950Notes

Reaction equation

HRID 1469950 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH2:10].[Br:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16]>>[BrH:11].[CH3:16][O:15][CH2:14][CH2:13][CH2:12][N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][C:2]1=[NH:10]

Participants

3

Reactant 2

HCID 8706Benzo(d)thiazol-2-amineHCID 5245511-Bromo-3-methoxypropane

Product 1

HCID 668599343-(3-Methoxy-propyl)-3H-benzothiazol-2-ylideneamine hydrobromideYield 89%

Procedure

Benzothiazol-2-ylamine (1.0 g, 6.6 mmol) and 1-bromo-3-methoxy-propane (1.2 g, 7.9 mmol) were processed as described in Example 2A. Recrystallization from ethyl acetate afforded 1.7 g (89%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 1.90-2.02 (m, 2H), 3.18 (s, 3H), 3.39 (t, J=5.9 Hz, 2H), 4.31 (t, J=7.1 Hz, 2H), 7.37-7.48 (m, 1H), 7.53-7.69 (m, 2H), 8.00 (dd, J=8.0, 0.8 Hz, 1H), 10.08 (s, 1H); MS (DCI/NH3) m/z 233 (M+H)+.

Workup

  1. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b76595be0ba2450d9628119072a82bf6
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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