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

HRID 255068Notes

Reaction equation

HRID 255068 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].[CH3:11][O:12][CH2:13][CH2:14][Br:15]>>[BrH:15].[CH3:11][O:12][CH2:13][CH2:14][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 809722-Bromoethyl methyl ether

Product 1

HCID 668598093-(2-Methoxyethyl)-3H-benzothiazol-2-ylideneamine hydrobromideYield 82%

Conditions

Temperature
85 °C

Procedure

Benzothiazol-2-ylamine (10.0 g, 66.6 mmol) and 2-bromoethyl methyl ether (9.39 mL, 99.9 mmol) were combined and heated at 85° C. for 6 hours. The dark solid was triturated with EtOH then filtered and dried under vacuum to afford the title compound (15.8 g, 82%). 1H NMR (DMSO-d6, 300 MHz) δ ppm 3.23 (s, 3 H), 3.69 (t, J=5.1 Hz, 2 H), 4.51 (t, J=5.1 Hz, 2 H), 7.42 (dt, J=1.0, 8.0 Hz, 1 H), 7.56 (m, 1 H), 7.72 (d, J=8.0 Hz, 1 H), 8.00 (dd, J=1.1, 8.0 Hz, 1H), 10.16 (br s, 2 H); MS (DCI/NH3) m/z 209 (M+H)+.

Workup

  1. customThe dark solid was triturated with EtOH
  2. filtrationthen filtered
  3. customdried under vacuum

Sources & evidence

ORD record
ord-5243cd18fe9a4487802331da3149aa54
Source dataset
uspto-grants-2011_01
Patent number
US07875639B2

Reaction notes

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