Benzo(d)thiazol-2-amine → HCID 66860500, compound

HRID 255108Notes

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].[I:11][CH2:12][CH2:13][CH2:14][CH3:15]>>[IH:11].[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])[CH2:13][CH2:14][CH3:15]

Participants

Reactant 2

HCID 8706Benzo(d)thiazol-2-amine

HCID 10962Butyl iodide

Product 1

HCID 66860500HCID 66860500, compoundYield 63.5%

Procedure

Benzothiazol-2-ylamine (1.0 g, 6.6 mmol) and 1-iodobutane (0.90 mL, 7.9 mmol) were processed as described in Example 46A. Recrystallization from ethyl acetate provided 1.4 g (63%) of the title compound. 1H NMR (DMSO-d6, 300 MHz) δ ppm 0.92 (t, J=7.3 Hz, 3 H), 1.32-1.46 (m, 2 H), 1.60-1.73 (m, 2 H), 4.19-4.28 (m, 2 H), 7.40-7.47 (m, 1 H), 7.54-7.62 (m, 1 H), 7.73 (d, J=7.8 Hz, 1 H), 8.00 (dd, J=7.8, 1.0 Hz, 1 H), 10.00-10.13 (m, 1 H); MS (DCI/NH3) m/z 207 (M+H)+.

Workup

customRecrystallization from ethyl acetate

Sources & evidence

ORD record: ord-a531d3d3554340118c85106f44349abc
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07875639B2

Reaction notes

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