Phosphorus oxychloride → 5-(1-Chloro-2-methylpropan-2-yl)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 436682Notes

Reaction equation

HRID 436682 reaction equation
[CH3:1][NH:2][C:3](=[S:6])[NH:4][NH2:5].[Cl:7][CH2:8][C:9]([CH3:14])([CH3:13])[C:10](O)=O.P(Cl)(Cl)(Cl)=O>O1CCOCC1>[Cl:7][CH2:8][C:9]([C:14]1[S:6][C:3]([NH:2][CH3:1])=[N:4][N:5]=1)([CH3:13])[CH3:10]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 83542beta-Chloropivalic acidHCID 2723853N-Methylhydrazinecarbothioamide

Product 1

HCID 127696565-(1-Chloro-2-methylpropan-2-yl)-N-methyl-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

An 87.2 g. portion of 4-methylthiosemicarbazide and 113.2 g. of 3-chloro-2,2-dimethylpropionic acid were suspended in 300 ml. of dioxane. The mixture was heated to 90° C. and 139.5 g. of phosphorus oxychloride was added dropwise while holding the temperature constant. After the addition was complete, the reaction mixture was stirred at 90° C. for three hours. The mixture was then allowed to cool and stand overnight at room temperature.

Workup

  1. additionAfter the addition
  2. temperatureto cool
  3. waitstand overnight at room temperature

Sources & evidence

ORD record
ord-aee4a4e5815f4e63b86f62bb91b9377a
Source dataset
uspto-grants-1977_06
Patent number
US04028090

Reaction notes

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