Methane, dichloromethoxy- → HCID 22620096, compound

HRID 1459588Notes

Reaction equation

HRID 1459588 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][S:12][CH:13]=2)=[CH:5][CH:4]=1.[CH3:14][O:15]C(Cl)Cl.C(=O)(O)[O-].[Na+]>C(Cl)Cl.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[N:11][S:12][CH:13]=2)=[CH:5][C:4]=1[CH:14]=[O:15]

Participants

6

Reactant 3

HCID 21004Methane, dichloromethoxy-HCID 516892Sodium Bicarbonate2×HCID 27393494-(4-Methoxyphenyl)-1,2,3-thiadiazole

Product 1

HCID 22620096HCID 22620096, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 0.99 grams (5.15 mmol) of 4-(4-methoxyphenyl)-1,2,3-thiadiazole (Maybridge Chemical Co.) in 23 mL of anhydrous methylene chloride (CH2Cl2) cooled to 0° C., was treated with 2.3 mL (21.9 mmol) of titanium tetrachloride and stirred for 30 min. The red solution was treated with 0.97 mL (10.7 mmol) of α,α-dichloromethyl methyl ether and allowed to warm to room temperature overnight. The reaction mixture was then poured over 100 mL of saturated aqueous sodium bicarbonate (NaHCO3), the pH was adjusted to 7-8 with solid NaHCO3 and the solution was then extracted with CH2Cl2. The organic layer was dried with magnesium sulfate (MgSO4) and concentrated to a yellow solid. Chromatography on silica gel (20% EtOAc: 80% Hexane) gave the pure title compound as a light yellow solid, 0.35 g (31%).

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionthe solution was then extracted with CH2Cl2
  3. dry with materialThe organic layer was dried with magnesium sulfate (MgSO4)
  4. concentrationconcentrated to a yellow solid

Sources & evidence

ORD record
ord-0ddb04c8a71c4be9a1b77ea52f0f425d
Source dataset
uspto-grants-1998_12
Patent number
US05854262

Reaction notes

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