Ammonium thiocyanate → HCID 20130710, compound

HRID 845961Notes

Reaction equation

HRID 845961 reaction equation
BrBr.[S-:3][C:4]#[N:5].[NH4+].[Cl:7][C:8]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:26](=[O:27])[CH:25]=[C:24]([CH3:28])[NH:23][C:22]2=[O:29])=[CH:16][C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]>C(O)(=O)C>[Cl:7][C:8]1[CH:19]=[C:18]([F:20])[C:17]([N:21]2[C:26](=[O:27])[C:25]([S:3][C:4]#[N:5])=[C:24]([CH3:28])[NH:23][C:22]2=[O:29])=[CH:16][C:9]=1[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11]

Participants

5

Reactant 3

HCID 15666Ammonium thiocyanateHCID 24408BromineHCID 19994231HCID 19994231, compound

Product 1

HCID 20130710HCID 20130710, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent3×

Procedure

1.86 g of bromine in 10 ml of acetic acid are added dropwise with stirring to 2.1 g of ammonium thiocyanate in 80 ml of acetic acid at 10°-15° C. during 15 minutes. Then 1.5 g of isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-methyl-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate in 15 ml of acetic acid are added dropwise at 10°-15° C. during 5 minutes, and the reaction mixture is stirred for a further hour at room temperature and thereafter substantially evaporated under reduced pressure. The residue is dissolved in ethyl acetate, the solid material filtered off under suction and the filtrate washed with aqueous sodium bicarbonate solution and thereafter with water. The organic phase is dried over anhydrous sodium sulphate and evaporated to dryness under reduced pressure. The residue is purified by chromatography on a silica gel column using methylene chloride/ethyl acetate (3:1) as eluent. The product is recrystallized from methylene chloride/diethyl ether. Isopropyl 2-chloro-4-fluoro-5-[3,6-dihydro-4-methyl-5-thiocyanato-2,6-dioxo-1(2H)-pyrimidinyl]-benzoate, m.p. 159°-161° C., is obtained.

Workup

  1. customsubstantially evaporated under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. filtrationthe solid material filtered off under suction
  4. washthe filtrate washed with aqueous sodium bicarbonate solution
  5. dry with materialThe organic phase is dried over anhydrous sodium sulphate
  6. customevaporated to dryness under reduced pressure
  7. customThe residue is purified by chromatography on a silica gel column
  8. customThe product is recrystallized from methylene chloride/diethyl ether

Sources & evidence

ORD record
ord-75ab6b1124254c168b2e6c0ac6a98eb3
Source dataset
uspto-grants-1988_07
Patent number
US04760163

Reaction notes

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