Sodium Chloride → HCID 53934759, compound

HRID 1732409Notes

Reaction equation

HRID 1732409 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 hexamethylphosphorotriamide are then added dropwise at 0°-3° C. in the course of 1.5 hours. 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 and is then poured onto 1.5 liters of ice water and 0.5 liter of saturated sodium chloride solution. The solid obtained is filtered off and recrystallized from acetone. 11.8 g (51% of theory) of yellow crystals are obtained. Melting point 134°-135° C.

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. customThe solid obtained
  5. filtrationis filtered off
  6. customrecrystallized from acetone
  7. custom11.8 g (51% of theory) of yellow crystals are obtained

Sources & evidence

ORD record
ord-2eabdba7ac2c4458a58ea1e5cdf6a0ea
Source dataset
uspto-grants-1980_12
Patent number
US04237278

Reaction notes

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