2-Bromo-1,3,4-thiadiazole → HCID 70575073, compound

HRID 443378Notes

Reaction equation

HRID 443378 reaction equation
[Br:1]C1SC=NN=1.[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]3)=[CH:15][C:10]=2[S:9][CH2:8]1>C1(C)C(C)=CC=CC=1.CN(C)C=O>[BrH:1].[O:7]1[C:11]2[CH:12]=[CH:13][C:14]([CH2:16][N:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[CH:15][C:10]=2[S:9][CH2:8]1

Participants

5

Reactant 2

HCID 27951982-Bromo-1,3,4-thiadiazoleHCID 70575074HCID 70575074, compound

Product 1

HCID 70575073HCID 70575073, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 7237O-XyleneSolvent

Procedure

A solution of 4 g of 2-bromo-1,3,4 thiadiazole and 13 g of 1-[(2H)-1,3-benzoxathiol-5-yl methyl]piperazine in 200 ml of xylene and 10 ml of anhydrous dimethylformamide was refluxed for 3 hours. Then, the mixture was cooled, the crystals of 1-[(2H)-1,3-benzoxathiol-5-yl methyl]piperazine hydrobromide formed during the reaction were suctioned off, and the xylene filtrate was extracted several times with a 2 N solution of methane sulfonic acid. The acid layer was decanted off then rendered alkaline with an excess of potassium carbonate, and the raw base extracted with chloroform. The organic solution was washed with water, dried over dry potassium carbonate, and the solvent was evaporated off. There were obtained 8 g of an oily residue which was submitted to a high pressure liquid chromatography (Waters apparatus) in the system CH2Cl2 -methanol; 98-2.

Workup

  1. temperatureThen, the mixture was cooled

Sources & evidence

ORD record
ord-72b1373a2f194a85be7c9f3ea78340df
Source dataset
uspto-grants-1981_04
Patent number
US04260610

Reaction notes

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