Phosphoric Acid → HCID 19073514, compound

HRID 865920Notes

Reaction equation

HRID 865920 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 45 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. customto come to room temperature
  2. additionare added
  3. extractionextracted with methyl tert-butyl ether
  4. washthe combined organic phases are carefully washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customwhich is chromatographed on silica gel

Sources & evidence

ORD record
ord-6101cdac76984c419f052947d203c43d
Source dataset
uspto-grants-1996_10
Patent number
US05569640

Reaction notes

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