Carbon Disulfide → 4-Amino-2-(butylsulfanyl)-1,3-thiazole-5-carbonitrile

HRID 477871Notes

Reaction equation

HRID 477871 reaction equation
[OH-].[K+].[N:3]#[C:4][NH2:5].[CH2:6](Br)[CH2:7][CH2:8][CH3:9].Cl[CH2:12][C:13]#[N:14].[C:15](=[S:17])=[S:16]>O.CN(C)C=O>[CH2:6]([S:17][C:15]1[S:16][C:12]([C:13]#[N:14])=[C:4]([NH2:5])[N:3]=1)[CH2:7][CH2:8][CH3:9]

Participants

8

Reactant 5

HCID 6348Carbon DisulfideHCID 7856ChloroacetonitrileHCID 8002Butyl bromideHCID 9864CyanamideHCID 14797Potassium Hydroxide

Product 1

HCID 542743064-Amino-2-(butylsulfanyl)-1,3-thiazole-5-carbonitrile

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A concentrated solution of 128 g of KOH in approximately 80 ml of water is slowly added dropwise to a solution of 42.0 g of cyanamide in approximately 500 ml of dimethyl formamide to which 90 ml (114 g) of carbon disulphide have been added. During the addition the mixture is stirred and kept at a temperature of 0°-10° C. by cooling. After 45 minutes, 107 ml (137 g) of n-butylbromide are slowly added dropwise while cooling and stirring and, after 30 minutes, 63.5 ml (75.5 g) of chloroacetonitrile are then added. The cooling bath is removed and, after stirring for another 30 minutes, a concentrated solution of 10 g of KOH in water is added, the temperature of the reaction mixture rising to approximately 60° C. After stirring for another hour at 60° C. the reaction mixture is poured in 2.5 l of ice water, after which the formed precipitate is sucked off, washed successively with water, isopropyl alcohol and petroleum ether, and dried. The desired product is obtained in a yield of 158.9 g and melts at 115°-117° C.

Workup

  1. additionhave been added
  2. additionDuring the addition the mixture
  3. customkept at a temperature of 0°-10° C.
  4. temperatureby cooling
  5. temperaturewhile cooling
  6. stirringstirring and, after 30 minutes
  7. customThe cooling bath is removed
  8. stirringafter stirring for another 30 minutes
  9. additiona concentrated solution of 10 g of KOH in water is added
  10. customrising to approximately 60° C
  11. stirringAfter stirring for another hour at 60° C. the reaction mixture
  12. additionis poured in 2.5 l of ice water
  13. washwashed successively with water, isopropyl alcohol and petroleum ether
  14. customdried

Sources & evidence

ORD record
ord-2976fd8460f44a4c8c2920c69b65b309
Source dataset
uspto-grants-1989_12
Patent number
US04889863

Reaction notes

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