Acetonitrile → HCID 54413364, compound

HRID 904808Notes

Reaction equation

HRID 904808 reaction equation
[CH3:1][N:2]1[C:6]([NH2:7])=[C:5]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]2=[N:3]1.C[N:16]=[C:17]=[O:18].[C:19](#N)C>>[CH3:1][N:2]1[C:6]([N:7]([CH3:19])[C:17]([NH2:16])=[O:18])=[C:5]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:4]2=[N:3]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 12228Methyl IsocyanateHCID 13282157HCID 13282157, compound

Product 1

HCID 54413364HCID 54413364, compound

Procedure

A solution of 2-methyl-2H-benzofuro[3,2-c]pyrazol-3-amine (4.0 g, 21.37 mmol, described in Example 6) in acetonitrile (150 mL) was combined with excess methyl isocyanate (ca. 6 mL) and the mixture was stirred at room temperature for several days. The precipitate was collected, washed with acetonitrile and diethyl ether to give the title compound (4.54 g) as off-white crystals: mp ca. 290° C. (dec.); IR (mineral oil) 3310, 3250, 1635, 1655, 1580 and 1525 cm-1 ; UV max (MeOH) 292 nm (ε=5656) and 269 (21000); NMR (DMSO-d6) δ2.65 (3H, d), 3.8 (3H, s), 6.4 (1H, m), 7.3 (3H, m), 7.8 (1H, m) and 8.35 (1H, s); and Anal. Calcd for C12H14N4O2 : C, 59.01% H, 4.95% N, 22.94% and Found: C, 58.96% H, 5.00% N, 22.62%.

Workup

  1. customThe precipitate was collected
  2. washwashed with acetonitrile and diethyl ether

Sources & evidence

ORD record
ord-fcd23151bb624868a7b0e2adb4196674
Source dataset
uspto-grants-1983_12
Patent number
US04420476

Reaction notes

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