2-Chloro-6-nitrobenzothiazole → HCID 21878473, compound

HRID 723958Notes

Reaction equation

HRID 723958 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([CH2:20][CH2:21][NH2:22])[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>O>[N:14]1([CH2:20][CH2:21][NH:22][C:2]2[S:3][C:4]3[CH:10]=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 754762-Chloro-6-nitrobenzothiazoleHCID 4082852-Morpholinoethylamine

Product 1

HCID 21878473HCID 21878473, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

To a mixture of 2-chloro-6-nitrobenzothiazole (1.00 g, 4.66 mmol) in water (9.0 mL) was added 2-morpholin-4-yl-ethylamine (2.45 mL, 18.6 mmol). The dark reaction mixture was stirred under argon and refluxed for 4.5 hours at which time the reaction became red-brown in colour. The mixture was then cooled to 65° C. and stirred an additional 17.75 hours. The precipitate was then collected by suction filtration after cooling to room temperature giving a yellow solid (377 mg, 26%). 1H NMR (DMSO-d6) δ: 8.69 (d, 1H, J=2.1 Hz), 8.10 (dd, 1H, J=2.1, 8.9 Hz), 7.46 (d, 1H, J=8.9 Hz), 3.59 (m, 6H), 2.55 (t, 2H, J=6.2 Hz), 2.51 (m, 4H), 2.43 (m, 4H).

Workup

  1. customThe dark reaction mixture
  2. temperaturerefluxed for 4.5 hours at which time the reaction
  3. stirringstirred an additional 17.75 hours
  4. filtrationThe precipitate was then collected by suction filtration
  5. temperatureafter cooling to room temperature

Sources & evidence

ORD record
ord-0374279fad294cc2bfec0c24864fc930
Source dataset
uspto-grants-2006_11
Patent number
US07141595B2

Reaction notes

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