Hydroxide → Cymiazole

HRID 1679168Notes

Reaction equation

HRID 1679168 reaction equation
[C:1]1([NH:9][C:10]([NH:12][CH3:13])=[S:11])[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][C:2]=1[CH3:8].C(OC(O[CH2:21][CH3:22])CCl)C.[OH-]>Cl>[C:1]1([N:9]=[C:10]2[N:12]([CH3:13])[CH:22]=[CH:21][S:11]2)[CH:6]=[CH:5][C:4]([CH3:7])=[CH:3][C:2]=1[CH3:8]

Participants

5

Reactant 3

HCID 961HydroxideHCID 121282-Chloro-1,1-diethoxyethaneHCID 30342141-(2,4-Dimethylphenyl)-3-methylthiourea

Product 1

HCID 43714Cymiazole

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

19.4 g (0.1 mole) of N-2,4-xylyl-N'-methyl-thiourea and 15.2 g (0.1 mole) of chloroacetaldehyde-diethylacetal in 150 ml of 2N aqueous hydrochloric acid are refluxed for 1 hour. The clear light-yellow solution is subsequently cooled to room temperature; it is rendered slightly alkaline with 30% aqueous medium hydroxide solution, and extracted with ether. The ether extract is washed with water, dried with sodium sulphate and filtered, and the ether is then distilled off. The oily residue is distilled; b.p. 132°-134° C/0.3 Torr; yield: 20.2 g = 92% of theory.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washis washed with water
  4. dry with materialdried with sodium sulphate
  5. filtrationfiltered
  6. distillationthe ether is then distilled off
  7. distillationThe oily residue is distilled

Sources & evidence

ORD record
ord-17326f4df40341ea967ed5534a26a618
Source dataset
uspto-grants-1978_03
Patent number
US04079144

Reaction notes

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