Phenacyl bromide → HCID 23463072, compound

HRID 2286338Notes

Reaction equation

HRID 2286338 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])=[N:5][N:6]=1.NNC(N)=S.ClC1C=CC=CC=1C(Cl)=O.Br[CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=O>CN(C)C=O>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:4]1[S:3][C:2]2=[N:1][C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[CH:30][N:6]2[N:5]=1

Participants

6

Reactant 4

HCID 6259Phenacyl bromideHCID 691102-Chlorobenzoyl chlorideHCID 5542115-(2-Chlorophenyl)-1,3,4-thiadiazol-2-amineHCID 2723789Thiosemicarbazide

Product 1

HCID 23463072HCID 23463072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.5 g (0.05 mol) of 2-amino-5-(2-chlorophenyl)-1,3,4-thiadiazole, melting point 189,5° C. (prepared by reacting thiosemicarbazide with 2-chlorobenzoyl chloride) together with 10 g (0.05 mol) of bromoacetophenone are warmed to 120° C. in 100 ml of dimethylformamide for 3 hours and the mixture is then cooled and concentrated in a rotary evaporator. After digesting the residue with water, the digestion mixture is filtered and the residue is recrystallised from alcohol. A second fraction is obtained by concentrating the alcoholic mother liquor. A total yield of 12.5 g, corresponding to 80% of theory, of colourless crystals of melting point 126° C. is obtained.

Workup

  1. temperaturethe mixture is then cooled
  2. concentrationconcentrated in a rotary evaporator
  3. filtrationthe digestion mixture is filtered
  4. customthe residue is recrystallised from alcohol
  5. customA second fraction is obtained
  6. concentrationby concentrating the alcoholic mother liquor
  7. customA total yield of 12.5 g, corresponding to 80% of theory, of colourless crystals of melting point 126° C. is obtained

Sources & evidence

ORD record
ord-9f593c31b76e42e983b3e5a8b3cec8a0
Source dataset
uspto-grants-1981_05
Patent number
US04265898

Reaction notes

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