Triethylamine → HCID 178477400, compound

HRID 584662Notes

Reaction equation

HRID 584662 reaction equation
[Cl:1][C:2]1[C:11]([CH2:12]Cl)=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[C:7]([Cl:14])[CH:8]=2)[N:3]=1.[SH:16][C:17]1[N:21](C)[N:20]=[N:19][N:18]=1.[CH2:23](N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[C:11]([CH:12]([S:16][C:17]2[NH:21][N:20]=[N:19][N:18]=2)[CH3:23])=[N:10][C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[C:7]([Cl:14])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 22341100HCID 22341100, compoundHCID 178482017HCID 178482017, compound

Product 1

HCID 178477400HCID 178477400, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,6,7-trichloro-3-chloromethylquinoxaline (500 mg, 1.78 mmol) in DMF (7 ml) was added 5-mercapto-1-methyltetrazole (206 mg, 1.78 mmol) followed by triethylamine (0.25 ml). The resulting dark reaction mixture was stirred at room temperature for 5 hours. Then it was partitioned between ethyl acetate and water. The organic layer was separated and concentrated to an oil. The oil was further purified by column chromatography (ethyl acetate:hexanes 1:2) to afford the title compound as a rusty powder.

Workup

  1. customThe resulting dark reaction mixture
  2. customThen it was partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. concentrationconcentrated to an oil
  5. customThe oil was further purified by column chromatography (ethyl acetate:hexanes 1:2)

Sources & evidence

ORD record
ord-1a6fb0c3a72d4cbca989e183fc066770
Source dataset
uspto-grants-2005_08
Patent number
US06927214B1

Reaction notes

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