Dimethylcarbamoyl Chloride → 2-Chloro-4-Isopropylamino-6-(2-[Dimethylcarbamylthio]ethylamino)-s-Triazine

HRID 2398052Notes

Reaction equation

HRID 2398052 reaction equation
[Na].C[O-].[Na+].[Cl:5][C:6]1[N:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[N:9]=[C:8]([NH:16][CH2:17][CH2:18][SH:19])[N:7]=1.[CH3:20][N:21]([CH3:25])[C:22](Cl)=[O:23]>CCOCC.CC(C)=O.CO>[Cl:5][C:6]1[N:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[N:9]=[C:8]([NH:16][CH2:17][CH2:18][S:19][C:22](=[O:23])[N:21]([CH3:25])[CH3:20])[N:7]=1

Participants

7

Reactant 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 214345132-Chloro-4-isopropylamino-6-(2-mercaptoethylamino)-s-triazine

Product 1

HCID 214345482-Chloro-4-Isopropylamino-6-(2-[Dimethylcarbamylthio]ethylamino)-s-Triazine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21584533Acetone diethyletherSolvent

Conditions

Temperature
80 °C

Procedure

A 0.46-g sample of sodium was added to 50 ml methanol in small pieces. To the resulting sodium methoxide solution was added 5 g of 2-chloro-4-isopropylamino-6-(2-mercaptoethylamino)-s-triazine, followed by 2.16 g dimethylcarbamyl chloride at 0° C. The reaction mixture was heated at 80° C. for 4 hours, cooled, filtered and evaporated under reduced pressure to give a yellow oil. The yellow oil was dissolved in 1:1 ether/acetone and filtered. The filtrate was evaporated to give the product as an oil. The elemental analysis on the product is tabulated in Table I.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. customevaporated under reduced pressure
  4. customto give a yellow oil
  5. filtrationfiltered
  6. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2727647c427f4caaa32af7e24ba1f0f0
Source dataset
uspto-grants-1977_05
Patent number
US04024141

Reaction notes

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