Triethylamine → HCID 53804495, compound

HRID 1438698Notes

Reaction equation

HRID 1438698 reaction equation
[CH3:1][N:2]([C:6](Cl)=[O:7])[C:3](Cl)=[O:4].I.[CH3:10][S:11][C:12](=[NH:18])[NH:13][N:14]=[C:15]([CH3:17])[CH3:16].C(N(CC)CC)C>C1C=CC=CC=1>[CH3:1][N:2]1[C:6](=[O:7])[NH:18][CH:12]([S:11][CH3:10])[N:13]([N:14]=[C:15]([CH3:17])[CH3:16])[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15555334N-Methylimidodicarbonic dichlorideHCID 178504061HCID 178504061, compound

Product 1

HCID 53804495HCID 53804495, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

15.6 g (0.1 mole) of N-methyl-bis-(chlorocarbonyl)-amine were dissolved in 100 ml of benzene and added dropwise, whilst stirring, to 27.3 g (0.1 mole) of acetone-S-methyliso-thio-semicarbazone hydroiodide suspended in 100 ml of benzene. Thereafter, 30.3 g (0.3 mole) of triethylamine in 50 ml of benzene were slowly added dropwise. The mixture was stirred for a further hour and the precipitate was filtered off. The precipitate was introduced into 100 ml of chloroform and 100 ml of water and extracted by shaking. The chloroform phase was separated off, dried over calcium chloride and evaporated in vacuo, together with the benzene filtrate. The resudue was recrystallized from isopropanol. 17.3 g (76%) of 1-methyl-3-isopropylideneamino-4-methylmercapto-tetrahydro-1,3,5-triazine-2,6-dione were obtained as a colorless powder; melting point 130-132° C.

Workup

  1. additionadded dropwise
  2. filtrationthe precipitate was filtered off
  3. additionThe precipitate was introduced into 100 ml of chloroform and 100 ml of water
  4. extractionextracted
  5. stirringby shaking
  6. customThe chloroform phase was separated off
  7. dry with materialdried over calcium chloride
  8. customevaporated in vacuo, together with the benzene filtrate
  9. customThe resudue was recrystallized from isopropanol

Sources & evidence

ORD record
ord-b0d566ef6d0f4810b43a904e84fdc2a9
Source dataset
uspto-grants-1977_11
Patent number
US04056527

Reaction notes

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