Sodium Chloride → HCID 53934759, compound

HRID 223374Notes

Reaction equation

HRID 223374 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 in the course of 1.5 hours, at 0°-3° C. Thereafter the mixture is stirred for 1 hour at room temperature and 11.7 g (0.085 mole) of dibromohydrin are then added dropwise. The solution is left to stand for 16 hours at room temperature and is then poured into 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. addition11.7 g (0.085 mole) of dibromohydrin are then added dropwise
  2. waitThe solution is left
  3. waitto stand for 16 hours at room temperature
  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-771156641b3148f69e115ae78d02b166
Source dataset
uspto-grants-1982_10
Patent number
US04353917

Reaction notes

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