Water → HCID 22902360, compound

HRID 1078364Notes

Reaction equation

HRID 1078364 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[S:13][N:12]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])[N:10]=2)[CH:6]=[CH:7][CH:8]=1.O.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[S:13][N:12]=[C:11]([O:14][CH2:15][CH2:16][CH2:17][Cl:18])[N:10]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 22902376HCID 22902376, compound

Product 1

HCID 22902360HCID 22902360, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2 g of 3-[5-(3-methoxyphenyl)-1,2,4-thiadiazole-3-oxy]-propyl chloride [for preparation, see Example 65 E)] were dissolved in 100 ml dichloromethane. A solution of 20 ml borotribromide in dichloromethane was added to the solution and the reaction mixture was stirred for 8 hours at room temperature under a nitrogen atmosphere. Then the reaction mixture was poured into water for workup and made alkaline by adding sodium carbonate. Then extraction was performed with dichloromethane and the organic phase was dried and concentrated. 1.9 g of crude 3-[5-(3-hydroxyphenyl)-1,2,4-thiadiazole-3-yloxy]-propyl chloride was obtained as a yellow oil.

Workup

  1. extractionThen extraction
  2. customthe organic phase was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-3869d2fd7bc64ac6a52fd0650534582f
Source dataset
uspto-grants-1996_08
Patent number
US05547967

Reaction notes

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