Isobutylamine → HCID 67241358, compound

HRID 2421837Notes

Reaction equation

HRID 2421837 reaction equation
[Cl:1][CH2:2][CH2:3][S:4][C:5]1[CH:13]=[CH:12][C:8]([C:9](Cl)=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15].[CH2:17]([NH2:21])[CH:18]([CH3:20])[CH3:19]>ClCCl.C([O-])(O)=O.[Na+]>[Cl:1][CH2:2][CH2:3][S:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([NH:21][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:10])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15]

Participants

5

Reactant 2

HCID 6558IsobutylamineHCID 86628742HCID 86628742, compound

Product 1

HCID 67241358HCID 67241358, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a biphasic solution of 4-(2-chloroethylthio)-3-nitrobenzoyl chloride (2.331 g, 8.32 mmol) in dichloromethane (75 mL) and saturated aqueous NaHCO3 (75 mL) was added isobutylamine (1.043 mL, 10.40 mmol). The reaction was allowed to stir for 16 hours. TLC and LCMS analysis of the reaction mixture indicated consumption of starting material. The reaction mixture was diluted with H2O (100 mL) and extracted with DCM (4×50 mL). The combined organics were dried over Na2SO4 and concentrated in vacuo. The product, 4-(2-chloroethylthio)-N-isobutyl-3-nitrobenzamide, was used without further purification. Product yield was assumed to be 100% (2.64 g, 8.32 mmol) for future calculations. LCMS (+ESI) m/z=317.13 [M+H]+.

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was diluted with H2O (100 mL)
  3. extractionextracted with DCM (4×50 mL)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe product, 4-(2-chloroethylthio)-N-isobutyl-3-nitrobenzamide, was used without further purification
  7. customProduct yield

Sources & evidence

ORD record
ord-7118a2e310e6400aacad222cd54bca46
Source dataset
uspto-grants-2011_06
Patent number
US07960376B2

Reaction notes

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