Dimethyl Sulfoxide → HCID 10519066, compound

HRID 863032Notes

Reaction equation

HRID 863032 reaction equation
[N+:1]([C:4]1[CH:23]=[CH:22][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][CH:13]([OH:17])[C:12]3[N:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(Cl)Cl.CS(C)=O.N1C(Cl)=NC(Cl)=NC=1Cl>O.C(N(CC)CC)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([N:10]2[CH2:16][CH2:15][CH2:14][C:13](=[O:17])[C:12]3[N:18]=[CH:19][CH:20]=[CH:21][C:11]2=3)=[O:9])=[CH:22][CH:23]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 7954Cyanuric chlorideHCID 10638906HCID 10638906, compound

Product 1

HCID 10519066HCID 10519066, compoundYield 125.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-25 °C

Procedure

A mixture of 0.313 g of 5-(4-nitrobenzoyl)-9-hydroxy-6,7,8,9-tetrahydro-5H-pyrido[3,2-b]azepine, 4 ml of CH2Cl2 and 0.75 ml of dimethylsulfoxide is chilled to -25° C. and 0.405 g of cyanuric chloride is added. The mixture is allowed to stand at -25° C. for 6.5 hours and 0.41 g of triethylamine is added. The mixture is stirred 10 minutes and poured into water. The mixture is extracted with dichloromethane and the extract washed with water, brine and dried (Na2SO4). The solvent is removed to give 0.39 g of solid. Chromatography on silica gel with ethyl acetate as solvent gives 0.17 g of crystals, m.p. 188°-190° C.

Workup

  1. extractionThe mixture is extracted with dichloromethane
  2. washthe extract washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is removed

Sources & evidence

ORD record
ord-0b95645684854e459918e5c8d749c77f
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

Loading…