5-Nitrothiophene-2-carboxaldehyde → HCID 178526537, compound

HRID 2218432Notes

Reaction equation

HRID 2218432 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[N:6][CH:7]=1.[N+:10]([C:13]1[S:17][C:16]([CH:18]=O)=[CH:15][CH:14]=1)([O-:12])=[O:11]>CN1C(=O)CCC1.[N+](C1C=CC=CC=1)([O-])=O.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]=[C:18]([C:16]3[S:17][C:13]([N+:10]([O-:12])=[O:11])=[CH:14][CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 782815-Nitrothiophene-2-carboxaldehydeHCID 12682545-Chloropyridine-2,3-diamine

Product 1

HCID 178526537HCID 178526537, compoundYield 25.4%

Reagents, catalysts & solvents 3

HCID 7416NitrobenzeneSolventHCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
170 °C

Procedure

5-Chloropyridine-2,3-diamine (4.0 g, 28 mmol) was dissolved in NMP (3 ml) and heated to 170° C. 5-Nitrothiophene-2-carbaldehyde (4.4 g, 28 mmol) dissolved in nitrobenzene (3 ml) and NMP (2 ml) was added slowly over 30 min. After 3 h, the reaction mixture was diluted with EtOAc and purified by dry flash chromatography (0%, 10%, 50%, 70% EtOAc in toluene), giving the title product (2 g, 25%).

Workup

  1. custompurified
  2. dry with materialby dry flash chromatography (0%, 10%, 50%, 70% EtOAc in toluene)

Sources & evidence

ORD record
ord-e3ddd2904591466dbe220ff99c3224e3
Source dataset
uspto-grants-2008_08
Patent number
US07410966B2

Reaction notes

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