Sodium Chloride → HCID 53934759, compound

HRID 444304Notes

Reaction equation

HRID 444304 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[CH:6]=[CH:7][C:8]1[S:9][C:10]([CH3:13])=[N:11][N:12]=1.[Cl-].[Na+].[O:20]1[CH2:24]C[CH2:22][CH2:21]1>CN(P(N(C)C)(N(C)C)=O)C>[CH3:13][C:10]1[S:9][C:8]([CH:7]=[CH:6][C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[O:3][CH2:22][CH:21]2[O:20][CH2:24]2)=[N:12][N:11]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 136139912HCID 136139912, compound

Product 1

HCID 53934759HCID 53934759, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

3.72 g (0.085 mole) of 55% strength sodium hydride in paraffin oil are suspended in 150 ml of absolute tetrahydrofuran and 18.6 g (0.085 mole) of 2-(2-hydroxystyryl)-5-methyl-1,3,4-thiadiazole in 200 ml of absolute hexamethylphosphotriamide are then added dropwise in the course of 1.5 hours at from 0° to 3° C. Stirring is continued at room temperature for 1 hour, after which 11.7 g (0.085 mole) of dibromohydrin are added dropwise. The solution is left to stand at room temperature for 16 hours, after which it is poured onto 1.5 liters of ice water and 0.5 liter of saturated sodium chloride solution. The precipitated solid is filtered off and recrystallized from acetone. 11.8 g (51% of theory) of yellow crystals, of melting point 134°-135° C. are obtained.

Workup

  1. additionafter which 11.7 g (0.085 mole) of dibromohydrin are added dropwise
  2. waitThe solution is left
  3. waitto stand at room temperature for 16 hours
  4. filtrationThe precipitated solid is filtered off
  5. customrecrystallized from acetone
  6. custom11.8 g (51% of theory) of yellow crystals, of melting point 134°-135° C. are obtained

Sources & evidence

ORD record
ord-6a247671397c4959b8dcda95fda621f5
Source dataset
uspto-grants-1981_04
Patent number
US04263430

Reaction notes

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