1-Pyrrolidineethanamine → 6-Nitro-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazole

HRID 723947Notes

Reaction equation

Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.[N:14]1([CH2:19][CH2:20][NH2:21])[CH2:18][CH2:17][CH2:16][CH2:15]1>>[N+:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:21][CH2:20][CH2:19][N:14]3[CH2:18][CH2:17][CH2:16][CH2:15]3)[S:3][C:4]=2[CH:10]=1)([O-:13])=[O:12]

Participants

Reactant 2

HCID 13441-Pyrrolidineethanamine

HCID 754762-Chloro-6-nitrobenzothiazole

Product 1

HCID 218784796-Nitro-2-(2-pyrrolidin-1-yl-ethylamino)benzothiazoleYield 20.6%

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-6-nitrobenzothiazole (250 mg, 1.16 mmol) and 2-pyrrolidin-1-yl-ethylamine (0.59 mL, 4.66 mmol) was heated at 100° C. for 4 hours then at 60° C. for 16 hours. After this time, the reaction mixture was filtered and the precipitate was washed with 2×5 mL of H2O. The solid was subjected to silica gel column chromatography (7.5% MeOH:92.5% CH2Cl2) to give the title compound as a yellow residue. Yield: 20.6%, 1H-NMR (DMSO-d6): δ 8.80 (br s, 1H); 8.70 (d, 1H, J=2.4 Hz); 8.11 (dd, 1H, J=6.8, 2.4 Hz); 7.47 (d, 1H, J=8.8 Hz); 3.58 (m, 2H); 2.60 (m, 6H); 1.73 (m, 2H).

Workup

filtrationAfter this time, the reaction mixture was filtered
washthe precipitate was washed with 2×5 mL of H2O

Sources & evidence

ORD record: ord-bd8c7f8682f24dd1bfbdb8a8404be144
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07141595B2

Reaction notes

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