Dichloromethane → HCID 20061639, compound

HRID 1085202Notes

Reaction equation

HRID 1085202 reaction equation
[O:1]=[C:2]1[NH:6][C:5]([C:7]([F:10])([F:9])[F:8])=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:3]1.[H-].[Na+].P(O)(O)([O-])=O.[Na+].C(Cl)Cl.O1C[CH2:30][CH2:29][CH2:28]1>>[O:1]=[C:2]1[N:6]([CH2:30][C:29]#[CH:28])[C:5]([C:7]([F:8])([F:9])[F:10])=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[S:3]1

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 2783041Ethyl 2-oxo-4-(trifluoromethyl)-2,3-dihydro-1,3-thiazole-5-carboxylateHCID 23672064Monosodium phosphate

Product 1

HCID 20061639HCID 20061639, compound

Procedure

6.9 g of ethyl 2,3-dihydro-2-oxo-4-trifluoromethyl-5-thiazole-carboxylate [prepared by the process of CA 92 110 998P]were dissolved in 70 ml of tetrahydrofuran at 0°±5° C. and then, 1.44 g of 50% sodium hydride in oil were added. Once the gaseous evolution ended, 15 ml of 2-bromopropyne were added and the mixture was refluxed for 48 hours. The mixture was poured on to an iced solution of monosodium phosphate and extraction was carried out with methylene chloride, then drying, filtering and concentrating under reduced pressure. The residue was chromatographed and elution with a hexane-ethyl acetate mixture (85-15) yielded 5.57 g of the expected product.

Workup

  1. temperaturethe mixture was refluxed for 48 hours
  2. customdrying
  3. filtrationfiltering
  4. concentrationconcentrating under reduced pressure
  5. customThe residue was chromatographed
  6. washelution with a hexane-ethyl acetate mixture (85-15)

Sources & evidence

ORD record
ord-ba94cf4f3f244cbb8ffa425c497b4bbf
Source dataset
uspto-grants-1991_04
Patent number
US05008281

Reaction notes

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