Water → HCID 57680507, compound

HRID 493072Notes

Reaction equation

HRID 493072 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH2:7]Br)([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2[CH2:30][S:29][C:28](=[O:31])[NH:27][N:26]=2)=[CH:21][CH:20]=1.O>C(#N)C>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[CH2:30][S:29][C:28](=[O:31])[N:27]([CH2:7][C:6]3[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=3)[N:26]=2)=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 3294735-(4-Chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one

Product 1

HCID 57680507HCID 57680507, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.19 g of 3-nitrobenzyl bromide and 9.95 g of potassium carbonate are added to a solution of 4.00 g of 5-(4-chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one in 80 ml of acetonitrile, and the mixture is stirred at 80° for a further 2 h. The mixture is poured into water, extracted 2× with diethyl ether, dried, filtered and evaporated to dryness. A little diethyl ether is added to the residue, which is crystallised and dried in a vacuum drying cabinet at 50° C., giving 5.5 g (86%) of 5-(4-chlorophenyl)-3-(3-nitrobenzyl)-3,6-dihydro-1,3,4-thiadiazin-2-one.

Workup

  1. extractionextracted 2× with diethyl ether
  2. customdried
  3. filtrationfiltered
  4. customevaporated to dryness
  5. additionA little diethyl ether is added to the residue, which
  6. customis crystallised
  7. customdried in a vacuum
  8. customdrying cabinet at 50° C.

Sources & evidence

ORD record
ord-719df263a80e476bb6634675d36e0469
Source dataset
uspto-grants-2009_05
Patent number
US07534785B2

Reaction notes

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