Pyridine → HCID 18176487, compound

HRID 394447Notes

Reaction equation

HRID 394447 reaction equation
[CH3:1][N:2]1[C:12](=[O:13])[C:6]2[S:7][CH2:8][CH2:9][NH:10][CH2:11][C:5]=2[CH:4]=[N:3]1.N1C=CC=CC=1.[N+:20]([C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)([O-:22])=[O:21]>O>[CH3:1][N:2]1[C:12](=[O:13])[C:6]2[S:7][CH2:8][CH2:9][NH:10][CH:11]([C:27](=[O:28])[C:26]3[CH:25]=[CH:24][C:23]([N+:20]([O-:22])=[O:21])=[CH:31][CH:30]=3)[C:5]=2[CH:4]=[N:3]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 85024-Nitrobenzoyl chloride2×HCID 18176473HCID 18176473, compound

Product 1

HCID 18176487HCID 18176487, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
57.5 °C

Procedure

To a suspension of 0.8 g (4.06 mmol) of 8-methyl-2,3,4,5-tetrahydro-9(8H)-pyridazino[4,5-b][1,5]thiazepinone in 8 ml of anhydrous pyridine 0.99 g (5.33 mmol) of 4-nitrobenzoyl chloride is added, whereafter the suspension is stirred for 18-20 hours at 55-60° C., while adding every 4 hours 0.5 g (2.54 mmol) of 4-nitrobenzoyl chloride. The reaction mixture is poured on 60 ml of icy water and extracted with 3×50 ml of dichloromethane. The organic phase is washed with 2×50 ml of 2 M hydrochloric acid solution, then with 30 ml of saturated sodium hydrogen carbonate solution and 2×60 ml of water. The organic phase is dried, filtered and evaporated. The residue is purified by column chromatography. In this way 1.08 g (77%) of the title compound is obtained with a melting point of 230-232° C.

Workup

  1. additionis added, whereafter the suspension
  2. extractionextracted with 3×50 ml of dichloromethane
  3. washThe organic phase is washed with 2×50 ml of 2 M hydrochloric acid solution
  4. customThe organic phase is dried
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by column chromatography

Sources & evidence

ORD record
ord-c84a502d309540898e42be38d94185b1
Source dataset
uspto-grants-2003_08
Patent number
US06602865B1

Reaction notes

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