1,2-Ethanediamine, N1,N1,N2-trimethyl- → N,N,N'-Trimethyl-N'-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamine

HRID 1174906Notes

Reaction equation

HRID 1174906 reaction equation
Br[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.[CH3:14][NH:15][CH2:16][CH2:17][N:18]([CH3:20])[CH3:19]>C1COCC1.C(Cl)Cl>[CH3:19][N:18]([CH3:20])[CH2:17][CH2:16][N:15]([CH3:14])[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

Participants

5

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 116230402-Bromo-6-nitrobenzothiazole

Product 1

HCID 57771682N,N,N'-Trimethyl-N'-(6-nitro-benzothiazol-2-yl)ethane-1,2-diamineYield 100%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Suspend 2-bromo-6-nitrobenzthiazole (5.00 g, 19.3 mmol) in THF (150 mL). Add N,N, N-trimethylethylene diamine (5.2 g, 40.0 mmol) and stir at room temperature for 6 h. Dilute with CH2Cl2, wash with saturated sodium bicarbonate (2×) and brine, and concentrate in vacuo to afford the crude title compound (5.79 mg, 100%). Carry the crude product on as is. 1H NMR (400 MHz, CDCl3): δ 8.50 (d, 1H, J=2.2 Hz), 8.19 (dd, 1H, J=8.8, 2.2 Hz), 7.49 (d, 1H, J=9.2 Hz), 3.73 (m, 2H), 3.27 (s, 3H), 2.64 (t, 2H, J=6.8 Hz), 2.33 (s, 6H).

Workup

  1. washwash with saturated sodium bicarbonate (2×) and brine
  2. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-d7fef681a233499c9a30bb5aa4edc3bd
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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