Diisopropylethylamine → 4-(Benzo[d]thiazol-2-ylmethoxy)-N-(4-bromobenzyl)-2-nitroaniline

HRID 2178491Notes

Reaction equation

F[C:2]1[CH:18]=[CH:17][C:5]([O:6][CH2:7][C:8]2[S:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].Cl.[Br:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C>C(#N)C>[S:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[CH2:7][O:6][C:5]1[CH:17]=[CH:18][C:2]([NH:29][CH2:28][C:27]2[CH:30]=[CH:31][C:24]([Br:23])=[CH:25][CH:26]=2)=[C:3]([N+:19]([O-:21])=[O:20])[CH:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-((4-fluoro-3-nitrophenoxy)methyl)benzo[d]thiazole (1.9 g, 6.4 mmol), 4-bromobenzylamine hydrochloride (2.1 g, 9.6 mmol), DIPEA (5.5 mL, 31.9 mmol) and acetonitrile (10 mL) was added to a sealed tube and heated to reflux for 16 h. The reaction was cooled to 0° C. and solid product precipitated. Solids were collected by vacuum filtration, washed with cold acetonitrile (10 mL) and dried in vacuum oven at 60° C. This material was used without purification. MS (ESI): mass calcd. for C21H16BrN3O3S, 469.10; m/z found, 470.1 [M+H]+. 1H-NMR (500 MHz, DMSO-d6) δ 8.67-8.53 (m, 1H), 8.12 (d, J=7.9, 1H), 8.02 (d, J=8.1, 1H), 7.74 (d, J=3.1, 1H), 7.56-7.52 (m, 2H), 7.48-7.43 (m, 1H), 7.37-7.34 (m, 1H), 7.31 (d, J=8.4, 2H), 6.89 (d, J=9.5, 1H), 5.58 (s, 2H), 4.60 (d, J=6.2, 2H).

Workup

temperatureheated
temperatureto reflux for 16 h
customsolid product precipitated
filtrationSolids were collected by vacuum filtration
washwashed with cold acetonitrile (10 mL)
customdried in vacuum oven at 60° C
customThis material was used without purification

Sources & evidence

ORD record: ord-3fd19028b7d04e2e8251834c1e927553
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067917B2

Reaction notes

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