Sodium Acetate → 1,5‐Dimethyl‐6‐sulfanylidene‐3‐(2,2,7‐trifluoro‐3‐ oxo‐3,4‐dihydro‐2H‐1,4‐benzoxazin‐6‐yl)‐1,3,5‐ triazinane‐2,4‐dione

HRID 1480035Notes

Reaction equation

HRID 1480035 reaction equation
[CH3:1][N:2]([C:7](=[S:10])[NH:8][CH3:9])[C:3](=O)[O:4]C.C([O-])(=O)C.[Na+].[F:16][C:17]1([F:39])[O:22][C:21]2[CH:23]=[C:24]([F:37])[C:25]([NH:27][C:28](=[O:36])OC3C=CC=CC=3)=[CH:26][C:20]=2[NH:19][C:18]1=[O:38]>CN(C=O)C>[CH3:1][N:2]1[C:7](=[S:10])[N:8]([CH3:9])[C:28](=[O:36])[N:27]([C:25]2[C:24]([F:37])=[CH:23][C:21]3[O:22][C:17]([F:16])([F:39])[C:18](=[O:38])[NH:19][C:20]=3[CH:26]=2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 90039554HCID 90039554, compoundHCID 90039746HCID 90039746, compound

Product 1

HCID 1176617631,5‐Dimethyl‐6‐sulfanylidene‐3‐(2,2,7‐trifluoro‐3‐ oxo‐3,4‐dihydro‐2H‐1,4‐benzoxazin‐6‐yl)‐1,3,5‐ triazinane‐2,4‐dioneYield 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
60 °C

Procedure

0.97 g (5.0 mmol) methyl N-methyl-N-(methylcarbamothioyl)carbamate with a purity of 83.3% was dissolved in 4.2 g DMF. 0.14 g (1.7 mmol) sodium acetate was added. The mixture was stirred at 60° C. at a pressure of 25 mbar. Via syringe a solution of 1.32 g (3.7 mmol) phenyl N-(2,2,7-trifluoro-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)carbamate (purity 95.7%) in 4.2 g DMF was added within 2 h. From time to time fresh DMF was added to maintain the solvent volume. After a poststirring period of 1 h, a chemical yield 73% was determined by quantitative HPLC analytics (HPLC-method A; tR=4.9 min) of the product solution.

Workup

  1. temperatureto maintain the solvent volume

Sources & evidence

ORD record
ord-525ed56a9a714e6ab9744ecefe8486c6
Source dataset
uspto-grants-2016_08
Patent number
US09409894B2

Reaction notes

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