Water → HCID 13389311, compound

HRID 280097Notes

Reaction equation

HRID 280097 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[N:5][N:6]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.O.[OH-].[Na+]>CN(C)C=O>[CH2:9]([N:8]([CH2:7][C:4]1[S:3][C:2]2=[N:1][C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:14][N:6]2[N:5]=1)[CH2:11][CH3:12])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 14798Sodium HydroxideHCID 13389310HCID 13389310, compound

Product 1

HCID 13389311HCID 13389311, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

18.6 g (0.1 mol) of 2-amino-5-diethylaminomethyl-1,3,4-thiadiazole and 19.9 g of ω-bromo-acetophenone in 70 mL of dimethylformamide are warmed at 150° C. for 3 hours. 150 ml of water are added to the cooled reaction mixture and the mixture is neutralised with 20% strength sodium hydroxide solution. The precipitate is filtered off with suction. After recrystallisation from acetonitrile, 11.5 g (40.2%) of melting point 138° C. remain.

Workup

  1. filtrationThe precipitate is filtered off with suction
  2. customAfter recrystallisation from acetonitrile, 11.5 g (40.2%) of melting point 138° C.

Sources & evidence

ORD record
ord-2f77c8183b0c4f9fb362e5318fe67677
Source dataset
uspto-grants-1986_05
Patent number
US04588723

Reaction notes

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