4-Aminobenzoic Acid → HCID 19981541, compound

HRID 1461121Notes

Reaction equation

HRID 1461121 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.Cl[CH2:12][C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14].N12CCCN=C1CCCCC2>C1C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH2:12][C:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[O:14])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9784-Aminobenzoic AcidHCID 16844Chloro-N,N-diethylacetamideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 19981541HCID 19981541, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-aminobenzoic acid (1.37 g. 0.01 mole), 2-chloro-N,N-diethylacetamide 2.0 ml, 0.015 mole) and 1.8-diazabicyclo[5.4.0]-undec-7-ene (1.52 g, 0.01 mole) in benzene (20 ml) was stirred at 80° C. for 4 h and then evaporated in vacuo. The residue was taken up in ethyl acetate. After washing with 5% sodium bicarbonate and water the ethyl acetate extract was dried and evaporated in vacuo leaving crude title compound. Recrystallization from ethanol-water gave 1.5 g (60%). Mp 135°-136° C.

Workup

  1. customevaporated in vacuo
  2. washAfter washing with 5% sodium bicarbonate and water the ethyl acetate
  3. extractionextract
  4. customwas dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-26d1936d93824b99844b7af65945dd43
Source dataset
uspto-grants-1991_12
Patent number
US05073641

Reaction notes

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