Triethylamine → HCID 18669726, compound

HRID 1059005Notes

Reaction equation

HRID 1059005 reaction equation
C[O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH3:11])=[CH:6][CH:5]=1.[C:13](Cl)(=[O:17])[CH:14]([CH3:16])[CH3:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:13]([N:10]([C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:12])=[O:2])=[CH:5][CH:6]=1)[CH3:11])(=[O:17])[CH:14]([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 140375Methyl 4-methylaminobenzoate

Product 1

HCID 18669726HCID 18669726, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

4-Methylamino-benzoic acid methyl ester (0.41 g) were suspended in chloroform (20 ml). Isobutyryl chloride (0.79 g) in chloroform (10 ml) was added dropwise for 30 minutes and then dropwise triethylamine (1 ml) dissolved in chloroform (5 ml). The reaction mixture was stirred for 3 hours and the solvent was evaporated. 1M NaOII(aq) (40 ml) was added and the mixture stirred overnight. The solution was filtered to remove unsolved material and then acidified with 2M HCl(aq). Filtration and drying in vacuum yielded 0.48 g of the title product.

Workup

  1. customthe solvent was evaporated
  2. addition1M NaOII(aq) (40 ml) was added
  3. stirringthe mixture stirred overnight
  4. filtrationThe solution was filtered
  5. customto remove unsolved material
  6. filtrationFiltration
  7. customdrying in vacuum

Sources & evidence

ORD record
ord-344d191a08c0421cb0fd60ec7e8c5edb
Source dataset
uspto-grants-2003_02
Patent number
US06518312B2

Reaction notes

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