Water → 3-Phenylpyrimidine-2,4(1H,3H)-dione

HRID 1809279

Reaction equation

HRID 1809279 reaction equation
Cl[C:2]1[CH:18]=[C:17](F)[C:16]([N:20]2[C:25](=[O:26])[CH:24]=[C:23](C(F)(F)F)[NH:22][C:21]2=[O:31])=[CH:15][C:3]=1C(NS(N(C)C(C)C)(=O)=O)=O.S(OC)(OC)(=O)=O.O.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.C1COCC1>[C:16]1([N:20]2[C:25](=[O:26])[CH:24]=[CH:23][NH:22][C:21]2=[O:31])[CH:15]=[CH:3][CH:2]=[CH:18][CH:17]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 11329250Saflufenacil-N-desmethyl

Product 1

HCID 138630213-Phenylpyrimidine-2,4(1H,3H)-dione

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

50.0 g (0.098 mol) of 2-chloro-5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4-fluoro-N-{[methyl(1-methylethyl)amino]sulfonyl}benzamide, 3.2 g (0.0089 mol) of tetrabutylammonium bromide (=TBAB) and 15.1 g (0.12 mol) of dimethyl sulfate were introduced into the reaction vessel at 25° C. in a mixture of toluene, water and THF, and the mixture was heated to 40° C. Thereafter, a pH of 5.3-5.5 was established in the reaction mixture by addition of aqueous 10% strength NaOH solution. During the entire duration of the reaction, more aqueous 10% strength NaOH solution was added so that the pH during the entire course of the reaction was constantly at the pH which had been established beforehand. After the reaction had ended, stirring of the reaction mixture was continued for 3.5 h at 40° C. The phases were subsequently separated.

Workup

  1. additionwas added so that the pH during the entire course of the reaction
  2. customThe phases were subsequently separated

Sources & evidence

ORD record
ord-397b50e6bcb84bc0af2e5b2267ee1c98
Source dataset
uspto-grants-2013_01
Patent number
US08362026B2

Linked notes

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