Hydrochloric Acid → N,N'-Bis(4-ethoxycarbonylphenyl)benzamidine hydrochloride

HRID 1085759

Reaction equation

HRID 1085759 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[Cl:13][C:14](Cl)(Cl)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)(Cl)Cl.Cl>C1(C)C(C)=CC=CC=1>[ClH:13].[CH2:9]([O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:14](=[N:1][C:2]2[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:11][CH:12]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][CH:11]=1)=[O:7])[CH3:10]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2337BenzocaineHCID 6212ChloroformHCID 7367Benzotrichloride

Product 1

HCID 20058838N,N'-Bis(4-ethoxycarbonylphenyl)benzamidine hydrochloride

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred suspension of ethyl 4-aminobenzoate (165.0 g; 1.0 mole) in xylene (465 mL) was added α,α,α-trichlorotoluene (100.7 g; 0.52 mole). The mixture was allowed to reflux for 18 h, then was cooled to 0° C. and filtered. The resultant precipitate was washed with ice-cold xylene (2×70 mL), triturated with hot toluene and dried to yield the salt (89.8 g; 39.7%) as white crystals: mp 214.0°-215.5° C. 1H-NMR (CDCl3) 8.0-6.9 (m, 14H), 4.3 (q, 4H, J=7 Hz), 1.4 (t, 6H, J=7 Hz); IR (CHCl3) 1715, 1600; MS (m/e) 416 (M+ -HCl), 252 (base).

Workup

  1. temperatureto reflux for 18 h
  2. filtrationfiltered
  3. washThe resultant precipitate was washed with ice-cold xylene (2×70 mL)
  4. customtriturated with hot toluene
  5. customdried
  6. customto yield the salt (89.8 g; 39.7%) as white crystals

Sources & evidence

ORD record
ord-d1b83bc356334d40a64c1061327d25d2
Source dataset
uspto-grants-1991_04
Patent number
US05011628

Linked notes

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