Dimethyl-1,3,5-triazin-2-amine → N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide

HRID 1704611Notes

Reaction equation

HRID 1704611 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([N:20]=[C:21]=[O:22])(=[O:19])=[O:18]>C(#N)C>[CH3:9][C:4]1[N:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:21]([NH:20][S:17]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[Cl:10])(=[O:18])=[O:19])=[O:22])[N:3]=1

Participants

4

Reactant 2

HCID 15820Dimethyl-1,3,5-triazin-2-amineHCID 174071Benzenesulfonyl isocyanate, 2-chloro-

Product 1

HCID 13883435N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 12.3 g of 2-amino-4,6-dimethyl-1,3,5-triazine in 200 ml of acetonitrile was added with stirring 21.7 g of 2-chlorobenzenesulfonyl isocyanate. All of the solid dissolved after the reagents were added and the mixture was then evaporated to dryness. The solid residue was triturated with ethyl ether and isolated by filtration to give impure N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2-chlorobenzenesulfonamide melting at 115°-118° C. The nuclear magnetic resonance absorption spectrum of this product, in trifluoroacetic acid, showed singlet peaks at 2.69 and 2.9 parts per million.

Workup

  1. dissolutionAll of the solid dissolved after the reagents
  2. additionwere added
  3. customthe mixture was then evaporated to dryness
  4. customThe solid residue was triturated with ethyl ether
  5. customisolated by filtration

Sources & evidence

ORD record
ord-903d03d780f1417ea07cca14fe89c1a4
Source dataset
uspto-grants-1978_11
Patent number
US04127405

Reaction notes

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