N,N'-Dimethylethylenediamine → HCID 57771690, compound

HRID 1174942Notes

Reaction equation

HRID 1174942 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.[CH3:14][NH:15][CH2:16][CH2:17][NH:18][CH3:19]>C1COCC1>[CH3:14][N:15]([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)[CH2:16][CH2:17][NH:18][CH3:19]

Participants

4

Reactant 2

HCID 8070N,N'-DimethylethylenediamineHCID 754762-Chloro-6-nitrobenzothiazole

Product 1

HCID 57771690HCID 57771690, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 2-chloro-6-nitro-benzothiazole (2.20 g, 10.3 mmol) in THF (50 mL). Add N,N′-dimethyl-ethane-1,2-diamine (10.0 mL) and stir overnight at room temperature. Concentrate the reaction mixture in vacuo (adsorbing onto silica gel). Subject the mixture to silica gel flash column chromatography (120 g column, eluting with 10% 2N NH3 in MeOH/CH2Cl2) to yield the desired product (0.500 g, 18%). mass spectrum (m/e): 267.3 (M+1).

Workup

  1. concentrationConcentrate the reaction mixture in vacuo (adsorbing onto silica gel)
  2. washto silica gel flash column chromatography (120 g column, eluting with 10% 2N NH3 in MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9deacd60d71d4808aa3349b46b18b750
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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