Hexane → HCID 13135276, compound

HRID 2412371Notes

Reaction equation

HRID 2412371 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[CH:10]12[O:22][CH:13]([CH2:14][CH:15]1[S:16]([N:19]=[C:20]=[O:21])(=[O:18])=[O:17])[CH:12]=[CH:11]2.CCCCCC>ClCCl>[CH3:9][C:4]1[CH:5]=[C:6]([CH3:8])[N:7]=[C:2]([NH:1][C:20]([NH:19][S:16]([CH:15]2[CH:10]3[O:22][CH:13]([CH:12]=[CH:11]3)[CH2:14]2)(=[O:17])=[O:18])=[O:21])[N:3]=1

Participants

5

Reactant 3

HCID 8058HexaneHCID 130212-Amino-4,6-dimethyl pyrimidineHCID 20432171HCID 20432171, compound

Product 1

HCID 13135276HCID 13135276, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

30.7 g (0.25 mole) of 2-amino-4,6-dimethylpyrimidine were dissolved in 350 ml of dichloromethane and a solution of 52 g (0.26 mole) of 7-oxabicyclo[2.2.1]hept-2-en-6-ylsulfonyl isocyanate (Diels-Alder adduct of vinylsulfonyl isocyanate and furan) in 100 ml of dichloromethane was added at 0° C. with stirring. The mixture was stirred a further 12 hours at room temperature, cooled to 0° C. and n-hexane was added. The precipitated reaction product was filtered off with suction, washed with n-hexane and dried. 73.6 g (90.8% of theory) of N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-7-oxabicyclo[2.2.1]hept-2-en-6-ylsulfonamide having a melting point of 125°-145° C. were obtained.

Workup

  1. stirringThe mixture was stirred a further 12 hours at room temperature
  2. customThe precipitated reaction product
  3. filtrationwas filtered off with suction
  4. washwashed with n-hexane
  5. customdried

Sources & evidence

ORD record
ord-c59195d6daf149419bdce8d775a78a01
Source dataset
uspto-grants-1985_01
Patent number
US04492598

Reaction notes

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