Phosgene → HCID 22799517, compound

HRID 1834215Notes

Reaction equation

HRID 1834215 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:23]=[CH:24][C:25]=1[NH:26][C:27](=[O:29])C)[CH2:7][C:8]([NH:19]C(C)=O)(C(OCC)=O)[C:9]([O:11]CC)=[O:10])([O-])=O.C(Cl)([Cl:32])=O>>[ClH:32].[N:26]1[C:27](=[O:29])[N:1]=[C:4]2[CH:5]=[C:6]([CH2:7][C@@H:8]([C:9]([OH:11])=[O:10])[NH2:19])[CH:23]=[CH:24][C:25]=12

Participants

3

Reactant 2

HCID 6371PhosgeneHCID 13115711HCID 13115711, compound

Product 1

HCID 22799517HCID 22799517, compoundYield 54%

Procedure

Following the procedure for the production of the racemic mixture in Example 1, diethyl 2-(3-nitro-4-acetamidobenzyl)-2-acetaminomalonate is hydrolyzed and cyclized with phosgene to produce pure Example 3 title compound in 54% yield: m.p. 259° (decomp).

Sources & evidence

ORD record
ord-64719b00630a4d2cb7d76d4e3b39de22
Source dataset
uspto-grants-1978_01
Patent number
US04069333

Reaction notes

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