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Water → 1,3,4-Thiadiazole-2-carbonitrile, 5-(methylthio)-

HRID 1277928
Notes
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Reaction equation

HRID 1277928 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([NH2:10])=O)=[N:5][N:4]=1.C(N(CC)CC)C.O>C(Cl)(Cl)(Cl)Cl.O1CCCC1.[Ti](Cl)(Cl)(Cl)Cl>[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]#[N:10])=[N:5][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 13566351HCID 13566351, compound

Product 1

HCID 112406301,3,4-Thiadiazole-2-carbonitrile, 5-(methylthio)-

Reagents, catalysts & solvents 3

HCID 24193Titanium TetrachlorideCatalystHCID 5943Carbon Tetrachloride
Solvent
HCID 8028TetrahydrofuranSolvent2×

Procedure

350 ml tetrahydrofuran were added dropwise upon stirring and cooling at a temperature between 0° and 5° C. to a solution of 20 ml titanium tetrachloride in 50 ml carbon tetrachloride. There were then added at first in batches 15.3 g of 5-methylthio-1,3,4-thiadiazole-2-carboxamide as obtained in Example 11, and thereafter within a period of 1 hour 50 ml triethylamine which had been taken up in 50 ml tetrahydrofuran. After addition of 50 ml water the reaction mixture was extracted with chloroform. The extract was dried on magnesium sulfate and the solvent was removed in a vacuum. The residue was taken up in acetic acid ethylester and filtrated off from the insoluble residue. The ester phase was then treated with activated carbon and finally concentrated to dryness in a vacuum.

Workup

  1. customas obtained in Example 11
  2. extractionwas extracted with chloroform
  3. customThe extract was dried on magnesium sulfate
  4. customthe solvent was removed in a vacuum
  5. filtrationfiltrated off from the insoluble residue
  6. additionThe ester phase was then treated with activated carbon
  7. concentrationfinally concentrated to dryness in a vacuum

Sources & evidence

ORD record
ord-7136faf88f4a4341ba4c55251d85c8c8
Source dataset
uspto-grants-1981_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04279907

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes