Water → 2-Amino-4,5-diphenyl-3-furonitrile

HRID 1891029Notes

Reaction equation

HRID 1891029 reaction equation
C(NCC)C.[C:6]1([C:12]([CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)O)=[O:13])[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:22](#[N:26])[CH2:23][C:24]#[N:25].O>CN(C=O)C>[NH2:26][C:22]1[O:13][C:12]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:23]=1[C:24]#[N:25]

Participants

6

Reactant 4

HCID 962WaterHCID 8010MalononitrileHCID 8021DiethylamineHCID 8400Benzoin

Product 1

HCID 3896992-Amino-4,5-diphenyl-3-furonitrileYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Diethylamine (13.8 g) was added dropwise over a period of 30 min to a mixture of benzoin (10 g) and malononitrile (3.8 g) in DMF (30 ml) at 0° C. (the internal temperature should not exceed 40° C.). After the resulting mixture was stirred at room temperature for 16 h, water (100 mL) was added. The resulting precipitate was filtered, washed with sufficient amount of water, then with hexanes, and dried. The solid was recrystallized from ethanol to provide yellowish-brown solid product of the title compound (6 g, 49%). 1H NMR (300 MHz, CDCl3): δ 7.47-7.34 (m, 8H), 7.28-7.18 (m, 2H), 4.94 (br, 2H). LC-MS (ESI) m/z 261.1 (M+H).

Workup

  1. customexceed 40° C.
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with sufficient amount of water
  4. dry with materialwith hexanes, and dried
  5. customThe solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-bee077b6726145dfa51073e80b62c5ba
Source dataset
uspto-grants-2013_08
Patent number
US08507502B2

Reaction notes

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