Benzocaine → HCID 15734512, compound

HRID 1085765Notes

Reaction equation

[C:1]([C:5]1[CH:24]=[CH:23][C:8]([C:9]([NH:11][C:12]2[CH:22]=[CH:21][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:14][CH:13]=2)=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].P(Cl)(Cl)(Cl)(Cl)Cl.[NH2:31][C:32]1[CH:42]=[CH:41][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:34][CH:33]=1>>[CH2:19]([O:18][C:16]([C:15]1[CH:21]=[CH:22][C:12]([NH:11][C:9](=[N:31][C:32]2[CH:33]=[CH:34][C:35]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[CH:41][CH:42]=2)[C:8]2[CH:23]=[CH:24][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=2)=[CH:13][CH:14]=1)=[O:17])[CH3:20]

Participants

Reactant 3

HCID 2337Benzocaine

HCID 24819Phosphorus pentachloride

HCID 721207Ethyl 4-[[4-(1,1-dimethylethyl)benzoyl]amino]benzoate

Product 1

HCID 15734512HCID 15734512, compound

Procedure

N,N'-Bis(4-ethoxycarbonylphenyl)-4-t-butylbenzamidine (14) was prepared from ethyl 4-[N-(4-t-butylbenzoyl)]aminobenzoate, phosphorus pentachloride, and ethyl 4-aminobenzoate; yellow solid: mp 212°-219° C. 1H-NMR (CDCl3) 8.0-7.0 (m, 12H), 6.0 (br s, 1H), 4.3 (q, 4H, J=7 Hz), 1.4 (t, 6H, J=7 Hz), 1.3 (s, 9H); IR (Nujol) 3330, 1710, 1590; MS (m/e) 472 (M+), 308 (base).

Sources & evidence

ORD record: ord-ec8f284c9f0a4076a960a055abb82ac4
Source dataset: uspto-grants-1991_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05011628

Reaction notes

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