Dichloromethane → 1-[2-(1-Hydroxyethyl)phenylsulfamoyl]-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea

HRID 978934Notes

Reaction equation

HRID 978934 reaction equation
C(Cl)Cl.[CH3:4][C:5]1[N:10]=[C:9]([O:11][CH3:12])[N:8]=[C:7]([NH2:13])[N:6]=1.Cl[S:15]([N:18]=[C:19]=[O:20])(=[O:17])=[O:16].[OH:21][CH:22]([C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH2:26])[CH3:23]>C(OCC)C.C(N(CC)CC)C>[OH:21][CH:22]([C:24]1[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=1[NH:26][S:15]([NH:18][C:19]([NH:13][C:7]1[N:6]=[C:5]([CH3:4])[N:10]=[C:9]([O:11][CH3:12])[N:8]=1)=[O:20])(=[O:17])=[O:16])[CH3:23]

Participants

7

Reactant 4

HCID 6344Dichloromethane2×HCID 154662-Amino-4-methoxy-6-methyl-1,3,5-triazineHCID 70918Chlorosulfonyl isocyanateHCID 1120582-Amino-alpha-methylbenzenemethanol

Product 1

HCID 138538231-[2-(1-Hydroxyethyl)phenylsulfamoyl]-3-(4-methyl-6-methoxy-1,3,5-triazin-2-yl)urea

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8471TriethylamineSolvent

Procedure

To 75 milliliters of methylene chloride maintained at 0°-5° C. via an ice bath were added 1.4 grams of 4-methyl-6-methoxy-2-amino-1,3,5-triazine and 1.55 grams of chlorosulfonyl isocyanate. After stirring for 3 hours at ice bath temperature a methylene chloride solution containing 1.0 gram of triethylamine and 1.37 grams of 2-(1-hydroxyethyl)aniline was added dropwise. The reaction mixture was removed from the ice bath, allowed to stir an additional one-half hour and then poured into 100 milliliters of 2 percent aqueous hydrochloric acid solution. After phase separation, the organic layer was washed in water and concentrated on a rotary evaporator affording a dark oil. Addition of diethyl ether to the dark oil resulted in the formation of a precipitate which was filtered-off. The filtrate was evaporated and the residue was taken-up in chloroform and again evaporated affording a powdery solid. Vacuum drying afforded 1.7 grams of light tan solid confirmed by NMR analysis as the desired product.

Workup

  1. additionwas added dropwise
  2. customThe reaction mixture was removed from the ice bath
  3. additionpoured into 100 milliliters of 2 percent aqueous hydrochloric acid solution
  4. customAfter phase separation
  5. washthe organic layer was washed in water
  6. concentrationconcentrated on a rotary evaporator
  7. customaffording a dark oil
  8. customresulted in the formation of a precipitate which
  9. customThe filtrate was evaporated
  10. customagain evaporated
  11. customaffording a powdery solid
  12. customVacuum drying
  13. customafforded 1.7 grams of light tan solid

Sources & evidence

ORD record
ord-c8600088ccad46f585ae9454633ba89a
Source dataset
uspto-grants-1987_05
Patent number
US04666508

Reaction notes

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