Water → HCID 178519018, compound

HRID 1834193Notes

Reaction equation

HRID 1834193 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:3]=1[CH2:4]Cl.[C:11]([N:13]=[C:14]([S-:16])[S-:15])#[N:12].[K+].[K+].[OH2:19]>CO>[OH:19][C:11]1[N:13]=[C:14]([S:16][CH2:4][C:3]2[CH:6]=[CH:7][C:8]([Cl:10])=[CH:9][C:2]=2[Cl:1])[S:15][N:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 72122,4-Dichlorobenzyl chlorideHCID 83179Carbamodithioic acid, cyano-, dipotassium salt

Product 1

HCID 178519018HCID 178519018, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

72 g of 2,4-dichlorobenzyl chloride were added at 30° C to a mixture of 69.9 g of dipotassium N-cyanodithioimidocarbonate, 50 ml of water and 300 ml of methanol and the mixture was stirred at 30° C. for one-half hour. The methanol was evaporated under reduced pressure and 900 ml of water were added to the residue. 40 ml of 30% hydrogen peroxide were slowly added and the pH was kept basic by addition of potassium hydroxide. the mixture was stirred for 17 hours, was washed with ethyl acetate and was acidified with hydrochloric acid. The mixture was vacuum filtered and the precipitate was crystallized from toluene to obtain 32 g of 3-hydroxy-5-(2,4-dichlorobenzylthio)-1,2,4-thiadiazole melting at 134° C.

Workup

  1. customThe methanol was evaporated under reduced pressure and 900 ml of water
  2. additionwere added to the residue
  3. addition40 ml of 30% hydrogen peroxide were slowly added
  4. additionthe pH was kept basic by addition of potassium hydroxide
  5. stirringthe mixture was stirred for 17 hours
  6. washwas washed with ethyl acetate
  7. filtrationfiltered
  8. customthe precipitate was crystallized from toluene

Sources & evidence

ORD record
ord-c77b8abf7db44a2c8cfd9b45615cee19
Source dataset
uspto-grants-1978_01
Patent number
US04069319

Reaction notes

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