Dimethylformamide → HCID 14793453, compound

HRID 1461198Notes

Reaction equation

HRID 1461198 reaction equation
[H-].[Na+].[CH2:3]([C:13]1[CH:14]=[N:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=2)=[N:17][CH:18]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].C1(C)C=CC(S(O[CH:36](C)[CH:37]([C:42]#[N:43])[CH2:38][CH2:39][CH2:40][CH3:41])(=O)=O)=CC=1.[CH3:46]N(C)C=O>>[C:42]([C:37]([CH3:36])([CH2:38][CH2:39][CH2:40][CH3:41])[CH2:46][O:25][C:22]1[CH:21]=[CH:20][C:19]([C:16]2[N:17]=[CH:18][C:13]([CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[CH:14][N:15]=2)=[CH:24][CH:23]=1)#[N:43]

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 24758Sodium hydrideHCID 86745305HCID 86745305, compoundHCID 135585902Phenol, 4-(5-decyl-2-pyrimidinyl)-

Product 1

HCID 14793453HCID 14793453, compoundYield 48.8%

Conditions

Temperature
100 °C

Procedure

28 mg (0.7 mM) of sodium hydride and 1.5 ml of dimethylformamide were stirred, and 220 mg (0.7 mM) of p-(5-n-decyl-2-pyrimidyl)phenol was added, followed by stirring for 10 minutes. Further, 218 mg (0.7 mM) of 2-cyano-methylhexyl p-toluenesulfonate and dimethylformamide were added, followed by 6 hours of stirring under heating at 100° C. After the reaction, the solvent was distilled off and distilled water was added thereto, followed by extraction with diethyl ether. The organic layer was washed with distilled water and dried on sodium sulfate. After distilling off the solvent, the product was purified by thin layer chromatography (developer solvent: hexane/methylene chloride=1/5) to obtain 149 mg of 4-(5-n-decyl-2-pyrimidyl)-phenyl 2-cyano-2-methylhexyl ether. Yield: 48.8%, [α]25D -1.47 (C 1.494, methylene chloride) m.p.: 43° C.

Workup

  1. waitfollowed by 6 hours
  2. stirringof stirring
  3. customAfter the reaction
  4. distillationthe solvent was distilled off
  5. distillationdistilled water
  6. additionwas added
  7. extractionfollowed by extraction with diethyl ether
  8. washThe organic layer was washed with distilled water
  9. customdried on sodium sulfate
  10. distillationAfter distilling off the solvent
  11. customthe product was purified by thin layer chromatography (developer solvent: hexane/methylene chloride=1/5)

Sources & evidence

ORD record
ord-e362e1f50cc245029f80b1bbc032a963
Source dataset
uspto-grants-1991_12
Patent number
US05075031

Reaction notes

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