2-Amino-4-methoxy-6-methyl-1,3,5-triazine → 4-Bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-3-thiophenesulfonamide

HRID 1248384Notes

Reaction equation

HRID 1248384 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=1.[Br:11][C:12]1[C:13]([S:17]([N:20]=[C:21]=[O:22])(=[O:19])=[O:18])=[CH:14][S:15][CH:16]=1>O1CCCC1>[Br:11][C:12]1[C:13]([S:17]([NH:20][C:21]([NH:1][C:2]2[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([CH3:10])[N:3]=2)=[O:22])(=[O:18])=[O:19])=[CH:14][S:15][CH:16]=1

Participants

4

Reactant 2

HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 202157044-Bromothiophene-3-sulfonyl isocyanate

Product 1

HCID 132033344-Bromo-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-aminocarbonyl]-3-thiophenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
10 °C

Procedure

To 1.1 g of 2-amino-4-methoxy-6-methyl-1,3,5-triazine in 20 ml of tetrahydrofuran was added 2 g of 4-bromo-3-thiophenesulfonyl isocyanate in 5 ml of tetrahydrofuran. The mixture was then stirred and warmed on a steam bath for 15 minutes and allowed to stir at ambient temperature for 70 hours. It was then heated to reflux for 2 hours, cooled to 10° C., filtered and the filtrate evaporated. The residual oil was triturated to yield the desired product as a solid which after recrystallization from acetonitrile melted at 180°-183°, yield 1.5 g.

Workup

  1. temperaturewarmed on a steam bath for 15 minutes
  2. stirringto stir at ambient temperature for 70 hours
  3. temperatureIt was then heated
  4. temperatureto reflux for 2 hours
  5. filtrationfiltered
  6. customthe filtrate evaporated
  7. customThe residual oil was triturated

Sources & evidence

ORD record
ord-2ffbd682d14044bcb0f265d7670bc61e
Source dataset
uspto-grants-1985_06
Patent number
US04523943

Reaction notes

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