5-Isocyanato-2,3-dihydro-1-benzofuran → N-[2,3-Dihydrobenzofuran-5-yl]-N'-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]urea

HRID 1275021Notes

Reaction equation

HRID 1275021 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([N:10]=[C:11]=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[CH3:13][O:14][C:15]1[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][C:16]=1[N:22]1[CH2:27][CH2:26][N:25]([CH3:28])[CH2:24][CH2:23]1>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([NH:10][C:11]([NH:19][C:18]3[CH:20]=[CH:21][C:15]([O:14][CH3:13])=[C:16]([N:22]4[CH2:23][CH2:24][N:25]([CH3:28])[CH2:26][CH2:27]4)[CH:17]=3)=[O:12])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 27761565-Isocyanato-2,3-dihydro-1-benzofuranHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

Product 1

HCID 22118935N-[2,3-Dihydrobenzofuran-5-yl]-N'-[4-methoxy-3-(4-methylpiperazin-1-yl)phenyl]ureaYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2,3-dihydrobenzofuran-5-yl isocyanate (D3, 0.248 g, 1.5 mmol) in CH2Cl2 (20 ml) was added to a solution of 4-methoxy-3-(4-methylpiperazin-1-yl)aniline (EP 0533268A1, 0.309 g, 1.4 mmol) in CH2Cl2 (10 ml). After 18 hours a precipitate had formed which was filtered off, washed with CH2Cl2 and dried under vacuum to afford the title compound as a cream coloured solid (0.253 g, 47%).

Workup

  1. customAfter 18 hours a precipitate had formed which
  2. filtrationwas filtered off
  3. washwashed with CH2Cl2
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4af811ab70164ad0bfd5111573b0d2de
Source dataset
uspto-grants-2000_12
Patent number
US06159979

Reaction notes

Loading…