Diethyl Ether → HCID 22405341, compound

HRID 440791Notes

Reaction equation

HRID 440791 reaction equation
FC(F)(F)[C:3]([OH:5])=[O:4].[CH3:8][CH:9]([CH3:40])[CH2:10][N:11]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:15]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[N:14][CH:13]([NH:28][C:29]([NH:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=2)=[O:30])[C:12]1=[O:39].[CH3:41][C:42]1[CH:43]=C(N=C=O)C=C[CH:47]=1.CCOCC>O1CCCC1>[C:42]([O:5][C:3]([N:25]1[CH2:24][CH2:23][CH:22]([C:15]2[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[N:11]([CH2:10][CH:9]([CH3:40])[CH3:8])[C:12](=[O:39])[CH:13]([NH:28][C:29]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([CH3:38])[CH:33]=3)=[O:30])[N:14]=2)[CH2:27][CH2:26]1)=[O:4])([CH3:43])([CH3:47])[CH3:41]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 69303m-Tolyl isocyanateHCID 67746387HCID 67746387, compound

Product 1

HCID 22405341HCID 22405341, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the previous amino (0.35 g, 0.85 mmol) [Step 7] in anhydrous tetrahydrofuran (5 ml) was added 3-methylphenyl isocyanate (110 μl, 0.85 mmol) dropwise, under nitrogen. The resultant suspension was left to stand at room temperature for 1 h, after which time ether (20 ml) was added The solid was filtered off, washed with more ether and recrystallized from methanol to afford the title urea (290 mg, 62%) as a white solid. The mother liquors were evaporated and the residue chromatographed on silica gel, using 3:1 petrol-ethyl acetate followed by 1:1 petrol-ethyl acetate as the eluant. The product (103 mg, 22%) was isolated as a white solid; mp 202°-204° C. (MeOH); δH (360 MHz, CDCl3) 0.71 (3H, d, J=6.6 Hz), 0.78 (3H, d, J=6.6 Hz), 1.25-1.31 (1H, m), 1.43 (9H, s), 1.58-1.64 (2H, m), 1.73-1.77 (1H, m), 1.98-2.04 (1H, m), 2.31 (3H, m), 2.68-2.80 (2H, m), 2.91-2.98 (1H, m), 3.43 (1H, dd, J=13.8 and 5.1 Hz), 4.04-4.24 (2H, m), 4.29 (1H, dd, J=13.8 and 9.2 Hz), 5.33 (1H, d, J=6.5 Hz), 6.63 (1H, d, J=7.8 Hz), 6.70 (1H, s), 6.87 (1H, d, J=7.3 Hz), 7.08 (1H, d, J=8.1 Hz), 7.17 (1H, t, J=7.7 Hz), 7.20 (1H, s), 7.28 (1H, d, J=7.9 Hz), 7.36 (1H, d, J=8.0 Hz), 7.51 (1H, t, J=7.1 Hz), 7.56 (1H, d, J=7.9 Hz); m/z (CI, NH3) 547 (M+).

Workup

  1. filtrationwas filtered off
  2. washwashed with more ether
  3. customrecrystallized from methanol

Sources & evidence

ORD record
ord-059bdf3aacaa4639be5b38c70a3e4ae7
Source dataset
uspto-grants-1996_05
Patent number
US05521175

Reaction notes

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