Isobutylamine → HCID 2683040, compound

HRID 1531739Notes

Reaction equation

HRID 1531739 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[Cl:6][C:7]1[CH:15]=[CH:14][C:10]([C:11](Cl)=[O:12])=[CH:9][C:8]=1[N+:16]([O-:18])=[O:17].C(N(CC)CC)C>O1CCCC1>[CH2:1]([NH:5][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][C:7]([Cl:6])=[C:8]([N+:16]([O-:18])=[O:17])[CH:9]=1)[CH:2]([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6558IsobutylamineHCID 8471TriethylamineHCID 1234774-Chloro-3-nitrobenzoyl chloride

Product 1

HCID 2683040HCID 2683040, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

6 ml (0.06 mol) of isobutylamine in 60 ml tetrahydrofuran are added dropwise to a solution of 13.2 g (0.06 mol) of 4-chloro-3-nitro-benzoylchloride and 6 g (0.06 mol) of triethylamine in 150 ml tetrahydrofuran and the mixture is stirred for 1 hour. The solution is evaporated down, dissolved in methylene chloride and washed with water. The combined organic extracts are dried and evaporated down. The residue is chromatographed on silica gel and eluted with methylene chloride/ethanol (98:2). The desired fractions are combined and evaporated down.

Workup

  1. customThe solution is evaporated down
  2. dissolutiondissolved in methylene chloride
  3. washwashed with water
  4. customThe combined organic extracts are dried
  5. customevaporated down
  6. customThe residue is chromatographed on silica gel
  7. washeluted with methylene chloride/ethanol (98:2)
  8. customevaporated down

Sources & evidence

ORD record
ord-2a0e8b9672e84bcba45665a0f13bd067
Source dataset
uspto-grants-2001_03
Patent number
US06200976B1

Reaction notes

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