Pyridine → HCID 57771778, compound

HRID 1174943Notes

Reaction equation

HRID 1174943 reaction equation
[CH3:1][N:2]([C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)[CH2:3][CH2:4][NH:5][CH3:6].N1C=CC=CC=1.[C:25](Cl)(=[O:27])[CH3:26]>C(Cl)Cl>[CH3:6][N:5]([CH2:4][CH2:3][N:2]([CH3:1])[C:7]1[S:8][C:9]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:10]=2[N:11]=1)[C:25](=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 57771690HCID 57771690, compound

Product 1

HCID 57771778HCID 57771778, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dissolve N,N′-dimethyl-N-(6-nitro-benzothiazol-2-yl)-ethane-1,2-diamine (0.255 g, 0.957 mmol) in CH2Cl2 (10 mL) and add pyridine (0.1 mL, 1.2 mmol). Add acetyl chloride (0.102 mL, 1.43 mmol) and shake the mixture overnight at room temperature. Concentrate the reaction mixture in vacuo (adsorbing onto silica gel) and subject the mixture to silica gel flash column chromatography (40 g column, eluting with 1-10% MeOH/CH2Cl2) to yield the desired product (0.295 g, 100%). mass spectrum (m/e): 309.2 (M+1).

Workup

  1. customthe mixture overnight
  2. customat room temperature
  3. concentrationConcentrate the reaction mixture in vacuo (adsorbing onto silica gel)
  4. washto silica gel flash column chromatography (40 g column, eluting with 1-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ad80b674afb14981a040be82ebac4a08
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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