1-(3-Bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanone → 1-(3-Bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-2-hydroxyimino-ethanone

HRID 1375381Notes

Reaction equation

HRID 1375381 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)[CH:5]=[CH:6][CH:7]=1.[N:19]([O-])=[O:20].[Na+]>O1CCCC1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[C:9]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=2)=[N:19][OH:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 223220191-(3-Bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-ethanoneHCID 23668193Sodium Nitrite

Product 1

HCID 1363756141-(3-Bromophenyl)-2-(2-methylthiopyrimidin-4-yl)-2-hydroxyimino-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

12.75 g (39.5 mmol) C1 were dissolved in a mixture of 173 ml glacial acid, 136 ml tetrahydrofurane and 17 ml water. After cooling to 5° C. a solution of 3.24 g (47.0 mmol) sodium nitrite in 25 ml water was added keeping the temperature between 5° C. and 10° C. The cooling was removed and the mixture stirred for 6 hours at room temperature. After removal of the solvent in vacuo 320 ml water and 320 ml ethyl acetate were added. The pH was adjusted to 8 with 3 N NaOH. The phases were separated and the aqueous layer was extracted with 50 ml ethyl acetate. The combined organic layers were dried over sodium sulphate and the solvent was removed in vacuo. The residue was treated with diethylether, filtered off and dried. Yield: 8.33 g (60%) D1, m.p. 156–158° C.

Workup

  1. additionwas added
  2. customthe temperature between 5° C. and 10° C
  3. customThe cooling was removed
  4. customAfter removal of the solvent in vacuo 320 ml water and 320 ml ethyl acetate
  5. additionwere added
  6. customThe phases were separated
  7. extractionthe aqueous layer was extracted with 50 ml ethyl acetate
  8. dry with materialThe combined organic layers were dried over sodium sulphate
  9. customthe solvent was removed in vacuo
  10. additionThe residue was treated with diethylether
  11. filtrationfiltered off
  12. customdried

Sources & evidence

ORD record
ord-e54c58dedcd440b890a1241dbb21a5a9
Source dataset
uspto-grants-2007_01
Patent number
US07169781B2

Reaction notes

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