Dimethyl Sulfoxide → HCID 20312931, compound

HRID 2420074Notes

Reaction equation

HRID 2420074 reaction equation
[CH3:1][N:2]([OH:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=1[Cl:13])=[O:4].C(=O)([O-])[O-].[K+].[K+].CS(C)=O.Cl[CH:26](Cl)[CH3:27]>O>[CH3:1][N:2]1[C:3](=[O:4])[N:5]([C:6]2[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][C:7]=2[Cl:13])[CH2:27][CH2:26][O:14]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 63651,1-DichloroethaneHCID 11430Potassium CarbonateHCID 1491102HCID 1491102, compound

Product 1

HCID 20312931HCID 20312931, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of 11 g of N-methyl-N-hydroxy-N'-(2,4-dichlorophenyl)-urea, 55 g of potassium carbonate and 66 ml of dimethylsulfoxide was stirred for 20 minutes at 20° C and then 11 g of dichloroethane were added. The mixture was stirred for 16 hours at 20°-25° C and was then poured into water. The mixture was vacuum filtered and the recovered precipitate was taken up in ethyl acetate. The solution was dried and evaporated to dryness under reduced pressure. The residue was crystallized from isopropyl ether to obtain 8 g of 2-methyl-4-(2',4'-dichlorophenyl)-3-oxo-5,6-dihydro-1,2,4-oxadiazine melting at 94°-95° C.

Workup

  1. stirringThe mixture was stirred for 16 hours at 20°-25° C
  2. filtrationfiltered
  3. customThe solution was dried
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was crystallized from isopropyl ether

Sources & evidence

ORD record
ord-497c6e7cf94c4c9187e8fb89b3c2b7d1
Source dataset
uspto-grants-1978_08
Patent number
US04108993

Reaction notes

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