Phthalic Anhydride → Benzoic acid, 2-[[(1-phenylethyl)amino]carbonyl]-

HRID 1074422Notes

Reaction equation

[C:1]1(=[O:11])[O:6][C:4](=[O:5])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[C:12]1([CH:18]([NH2:20])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(O)(=O)C1C(=CC=CC=1)C(N)=O.C(C(O)C1C=CC=C(OC2C=CC=CC=2)C=1)#C>>[C:12]1([CH:18]([NH:20][C:4](=[O:5])[C:3]2[C:2](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:1]([OH:6])=[O:11])[CH3:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Reactant 4

HCID 6811Phthalic Anhydride

HCID 6957Phthalamic acid

HCID 74081-Phenethylamine

HCID 129190923-Phenoxy-alpha-ethynylbenzylalcohol

Product 1

HCID 571713Benzoic acid, 2-[[(1-phenylethyl)amino]carbonyl]-

Procedure

(-)-N-α-phenylethylphthalamic acid was prepared from phthalic anhydride and (-)α-phenylethylamine by the method of Mann and Wastom (J. Chem. Soc., 1947, 510). The ester of this phthalamic acid with racemic α-ethynyl-3-phenoxybenzyl alcohol was prepared by the method of Human and Mills (J. Chem. Soc., 1949, S77). The individual (-)(+) and (-)(-) ester diastereoisomers were separated by chromatography (HPLC) and then hydrolysed with a slight excess of alkali to recover the resolved α-ethynyl-3'-phenoxybenzyl alcohol.

Workup

customThe individual (-)(+) and (-)(-) ester diastereoisomers were separated by chromatography (HPLC)
customhydrolysed with a slight excess of alkali to recover the resolved α-ethynyl-3'-phenoxybenzyl alcohol

Sources & evidence

ORD record: ord-19fb0078446440dab4c6b58c0c3faff4
Source dataset: uspto-grants-1983_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04391820

Reaction notes

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