Phosphoric Acid → HCID 19073514, compound

HRID 1955992Notes

Reaction equation

HRID 1955992 reaction equation
Cl[C:2](=[N:4][OH:5])[CH3:3].C(N(CC)CC)C.[CH3:13][C:14]1([CH3:27])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([C:24]#[CH:25])[C:17]=2[C:16](=[O:26])[O:15]1.P(=O)(O)(O)O>C(OC)(C)(C)C.O>[CH3:13][C:14]1([CH3:27])[O:19][C:18]2[CH:20]=[CH:21][CH:22]=[C:23]([C:24]3[O:5][N:4]=[C:2]([CH3:3])[CH:25]=3)[C:17]=2[C:16](=[O:26])[O:15]1

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 8471Triethylamine2×HCID 69633Ethanimidoyl chloride, N-hydroxy-2×HCID 11989235HCID 11989235, compound

Product 1

HCID 19073514HCID 19073514, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

53 ml of the solution of 1-chloro-1-(N-hydroxyimino)ethane described above and 6.3 ml of triethylamine are added with stirring at 0° C. to a solution of 8.0 g of 2,2-dimethyl-5-(ethynyl)-4H-(1,3)benzodioxin-4-one in 400 ml of methyl tert-butyl ether, and the mixture is allowed to come to room temperature and is subsequently stirred overnight. A further 53 ml of the solution of 1-chloro-1-(N-hydroxyimino)ethane described above and 6.3 ml of triethylamine are added and the reaction solution is stirred at room temperature for 24 h. It is then poured into water containing phosphoric acid (pH 4) at 0° C. and extracted with methyl tert-butyl ether, and the combined organic phases are carefully washed with water, dried over sodium sulfate and concentrated. 8.8 g of crude product remain, which is chromatographed on silica gel using n-hexane/ethyl acetate. 4.1 g of colorless crystals are obtained, m.p. 74° C. (cf. Table 1, No. 1.020).

Workup

  1. additionare added
  2. customto come to room temperature
  3. additionare added
  4. extractionextracted with methyl tert-butyl ether
  5. washthe combined organic phases are carefully washed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customwhich is chromatographed on silica gel

Sources & evidence

ORD record
ord-36a5368ee9e34f218306cb0564f506f3
Source dataset
uspto-grants-1998_07
Patent number
US05777118

Reaction notes

Loading…