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Water → 5-(4-Chloro-phenyl)-3-(4-nitro-benzyl)-3,6-dihydro[1,3,4]thiadiazin-2-one

HRID 44283
Notes
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Reaction equation

HRID 44283 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:13][S:12][C:11](=[O:14])[NH:10][N:9]=2)=[CH:4][CH:3]=1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:13][S:12][C:11](=[O:14])[N:10]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=3)[N:9]=2)=[CH:6][CH:7]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 3294735-(4-Chlorophenyl)-3,6-dihydro-1,3,4-thiadiazin-2-one

Product 1

HCID 666367935-(4-Chloro-phenyl)-3-(4-nitro-benzyl)-3,6-dihydro[1,3,4]thiadiazin-2-one

Reagents, catalysts & solvents 1

HCID 6342
Acetonitrile
Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of the compound obtained in Step A (57.83 mmoles) in acetonitrile (260 ml) there are added 1-bromomethyl-4-nitro-benzene (63.61 mmoles) and potassium carbonate (231.32 mmoles). The reaction mixture is stirred at 80° C. for 1 hour under nitrogen. The reaction mixture is brought to ambient temperature and 100 ml of water are added. Extraction with ethyl ether (3×350 ml) is carried out and the organic phases are combined. The organic phase obtained is dried over sodium sulphate, filtered and evaporated to dryness. The solid is triturated in ethyl ether, filtered off and dried in vacuo to yield the title product, which is used directly in the next Step.

Workup

  1. customis brought to ambient temperature
  2. extractionExtraction with ethyl ether (3×350 ml)
  3. customThe organic phase obtained
  4. dry with materialis dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe solid is triturated in ethyl ether
  8. filtrationfiltered off
  9. customdried in vacuo

Sources & evidence

ORD record
ord-02652757b88b4162a185048b91d42468
Source dataset
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08541412B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes