3-Nitrobenzaldehyde → HCID 22597584, compound

HRID 1760493Notes

Reaction equation

HRID 1760493 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[N+:11]([C:14]1[CH:15]=[C:16]([CH:19]=[CH:20][CH:21]=1)[CH:17]=O)([O-:13])=[O:12].[C:22]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])#[N:23].O=P(Cl)(Cl)Cl.[SH:35][CH2:36][C:37](OCC)=O>CCCCCCC.CCOC(C)=O>[NH2:23][C:22]1[C:37]2[C:17]([C:16]3[CH:19]=[CH:20][CH:21]=[C:14]([N+:11]([O-:13])=[O:12])[CH:15]=3)=[N:9][C:8]([S:7][CH3:6])=[N:10][C:36]=2[S:35][C:24]=1[C:25]([O:27][CH2:28][CH3:29])=[O:26]

Participants

7

Reactant 5

HCID 74493-NitrobenzaldehydeHCID 7764Ethyl cyanoacetateHCID 12185Ethyl ThioglycolateHCID 24813Phosphorus oxychlorideHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 22597584HCID 22597584, compound

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

Cyclization of S-methylisothiourea sulfate (700 mg), 3-nitrobenzaldehyde (750 mg) and ethyl cyanoacetate (560 μl), treatment of the product with POCl3 and subsequent reaction with ethyl 2-mercaptoacetate were performed according to the methods described in example 1. The pure title compound was obtained after chromatography on silicagel in heptane/EtOAc=3/2 (v/v) as eluent.

Sources & evidence

ORD record
ord-502d37601e68407790ce127d88fddef9
Source dataset
uspto-grants-2005_01
Patent number
US06841553B2

Reaction notes

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