2-Amino-4-methoxy-6-methyl-1,3,5-triazine → N-2-biphenylylsulfonyl-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea

HRID 746148Notes

Reaction equation

HRID 746148 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[C:11]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[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.C1(C)C(C)=CC=CC=1.N12CCN(CC1)CC2>[C:11]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[S:17]([NH:20][C:21]([NH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1)=[O:22])(=[O:19])=[O:18]

Participants

6

Reactant 2

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 131033202-Biphenylylsulfonylisocyanate

Product 1

HCID 13103322N-2-biphenylylsulfonyl-N'-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)ureaYield 85%

Reagents, catalysts & solvents 3

HCID 9237DabcoCatalystHCID 6342AcetonitrileSolventHCID 7237O-XyleneSolvent

Procedure

14.0 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine were suspended in 100 ml of dry acetonitrile, and then 0.1 g of 1,4-diazabicyclo[2,2,2]octane was added thereto. To this mixture was added dropwise a solution of 28.5 g of 2-biphenylylsulfonyl isocyanate in 30 ml of xylene over an hour. During this addition, the reaction was accompanied by slight heat generation, and therefore cooling was applied as necessary. After the addition, the reaction was continued at room temperature for 5 hours and then at 40° C. for 5 hours. After allowing the mixture to cool to room temperature, the precipitated colorless crystals were filtered, washed with ether and dried to obtain 33.9 g of N-2-biphenylylsulfonyl-N'-(4-methoxy-6-methyl-1,3,5-triazin-2yl) urea; m.pt. 190°-193° C.

Workup

  1. additionDuring this addition
  2. temperaturecooling
  3. additionAfter the addition
  4. waitat 40° C. for 5 hours
  5. filtrationthe precipitated colorless crystals were filtered
  6. washwashed with ether
  7. customdried

Sources & evidence

ORD record
ord-028073f6362548f3982ca1d2cbcb8a09
Source dataset
uspto-grants-1986_07
Patent number
US04602941

Reaction notes

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