Acetonitrile → HCID 13369444, compound

HRID 1153940Notes

Reaction equation

HRID 1153940 reaction equation
[CH3:1][C:2]1[C:3]2[CH:10]=[C:9]([CH3:11])[O:8][C:4]=2[N:5]=[CH:6][N:7]=1.[C:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([N:25]=[C:26]=[O:27])(=[O:24])=[O:23])([O:14][CH3:15])=[O:13].C(#[N:30])C>>[CH3:1][C:2]1[C:3]2[CH:10]=[C:9]([CH3:11])[O:8][C:4]=2[N:5]=[C:6]([NH:30][C:26]([NH:25][S:22]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:12]([O:14][CH3:15])=[O:13])(=[O:23])=[O:24])=[O:27])[N:7]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 20435498HCID 20435498, compound

Product 1

HCID 13369444HCID 13369444, compound

Procedure

To a dry stirred solution of 0.5 g of 4,6-dimethylfuro[2,3-d]pyrimidin in 10 ml of acetonitrile at ambient temperature and pressure was added 1.6 g of 2-carbomethoxybenzenesulfonyl isocyanate. The resulting mixture was warmed on the steam bath for several minutes then stirred at ambient temperature for 4 hours. The suspended solid was collected by filtration and rinsed with acetonitrile to yield 0.87 g of methyl 2-{[(4,6-dimethylfuro[2,3-d]pyrimidin-2-yl)aminocarbonyl]aminosulfonyl}benzoate, m.p. 197°-198°. The product showed characteristic absorption bands at 1690 and 1735 cm-1 in the infrared spectrum and at 2.45, 2.75, 3.95, 6.6, 7.7, 8.3, 10.4 and 13.0 ppm in the nuclear magnetic resonance (60 MHz) spectrum indicating the title compound.

Workup

  1. temperatureThe resulting mixture was warmed on the steam bath for several minutes
  2. filtrationThe suspended solid was collected by filtration
  3. washrinsed with acetonitrile

Sources & evidence

ORD record
ord-f290c5549bd04ecfa5ec56a25c072f90
Source dataset
uspto-grants-1984_12
Patent number
US04487626

Reaction notes

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