Methane → HCID 19704698, compound

HRID 726945Notes

Reaction equation

HRID 726945 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]([N:12]1[CH2:17][CH2:16][O:15][CH2:14][NH:13]1)=[S:11].C(N(CC)CC)C.C.[C:26](Cl)(Cl)=[O:27]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]=[C:10]1[N:12]2[N:13]([CH2:14][O:15][CH2:16][CH2:17]2)[C:26](=[O:27])[S:11]1

Participants

6

Reactant 4

HCID 297MethaneHCID 6371PhosgeneHCID 8471TriethylamineHCID 19704695HCID 19704695, compound

Product 1

HCID 19704698HCID 19704698, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

1.8 g (6.2 mmol) N-(2,4-dichlorophenyl)tetrahydro-4H-1,3,4-oxadiazine-4-carbothioamide was dissolved in 30 mL toluene and 1 mL triethylamine in the presence of a small quantity of activated charcoal at 0°-5° C. 3.49 g (6.81 mmol) phosgene as 20% solution in 30 mL toluene was added dropwise over 1.5 h. The reaction mixture was then left to warm up to room temperature and stirred overnight. The activated charcoal was removed by filtration and the solvent evaporated in vacuo. The desired product was isolated after chromatography on silica gel.

Workup

  1. customat 0°-5° C
  2. waitThe reaction mixture was then left
  3. customThe activated charcoal was removed by filtration
  4. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-c4f5a530dfc141f285a5ffc96e12783a
Source dataset
uspto-grants-1998_01
Patent number
US05712225

Reaction notes

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