Water → HCID 12600751, compound

HRID 1489667Notes

Reaction equation

HRID 1489667 reaction equation
[C:1]1([C:7]2[S:11][N:10]=[C:9](OCCCCl)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O>ClCCl>[C:1]1([C:7]2[S:11][N:10]=[CH:9][N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 962WaterHCID 22902407HCID 22902407, compound

Product 1

HCID 12600751HCID 12600751, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

0.85 g of the product obtained above were reacted with 0.7 g of 3-(5-phenyl-1,2,4-thiadiazole-3-yloxy)-propyl chloride [for preparation, see Example 54B)] and the reaction mixture was stirred for 10.5 hours at 65° C. Then the reaction mixture was dissolved in dichloromethane and the solution shaken with water. The dichloromethane phase was separated, dried, and concentrated. The crude product obtained was purified by medium-pressure chromatography on fine-grained silica gel (Lichroprep Si 60®) using 9:1 ethyl acetate/methanol as the eluent. 0.5 g of 3-{3-[N-[2-(4-(2-trimethylsilyl)-ethoxymethoxy)-3-methoxyphenyl)-ethyl]-N-methylamino]-propyloxy}-5-phenyl-1,2,4-thiadiazole were obtained as a colorless oil.

Workup

  1. customfor preparation
  2. customThe dichloromethane phase was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe crude product obtained
  6. customwas purified by medium-pressure chromatography on fine-grained silica gel (Lichroprep Si 60®)

Sources & evidence

ORD record
ord-4c1b49943e264634bc269562cd2aeaf1
Source dataset
uspto-grants-1997_10
Patent number
US05679699

Reaction notes

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