Water → HCID 22902360, compound

HRID 1489663Notes

Reaction equation

HRID 1489663 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 65E)] 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-bf6bef9451ab4841a47d490121a85dcc
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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