N-methyl-2-phenoxyacetamide → HCID 21041753, compound

HRID 901888Notes

Reaction equation

HRID 901888 reaction equation
CC([O-])(C)C.[K+].[O:7]([CH2:14][C:15]([NH:17][CH3:18])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:19]([O:23][C:24](=[O:34])[C:25]1[CH:30]=[CH:29][C:28]([N:31]=[C:32]=[S:33])=[CH:27][CH:26]=1)[CH2:20][CH2:21][CH3:22]>C1COCC1>[CH2:19]([O:23][C:24](=[O:34])[C:25]1[CH:26]=[CH:27][C:28]([NH:31][C:32]([N:17]([CH3:18])[C:15](=[O:16])[CH2:14][O:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[S:33])=[CH:29][CH:30]=1)[CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 309654N-methyl-2-phenoxyacetamideHCID 8022494HCID 8022494, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 21041753HCID 21041753, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

t-BuOK (0.55 mL of 1.0 N solution) in THF is added to a solution of phenoxy-N-methylacetamide (83 mg, 0.5 mmol) in THF (5 mL). After 5 minutes, butyl-4-isothiocyanatobenzoate (118 mg, 0.5 mmol) is added in one portion and the resultant mixture is stirred overnight. The crude mixture is filtered through a silica pad. After purification on silica eluting with 25% EtOAc in hexane, the desired acylthiouraea is obtained as a yellow oil (20 mg). 1H NMR (300 MHz, CDCl3): δ 12.38 (s, 1H), 9.44 (s, 1H), 8.10 (d, 2H, J=8.7 Hz), 7.86 (d, 2H, J=6.9 Hz), 7.42-7.35 (m, 2H), 7.11 (t, 1H, J=7.4 Hz), 7.02-6.98 (m, 2H), 4.64 (s, 2H), 4.34 (t, 2H, J=6.6 Hz), 1.81-1.72 (m, 2H), 1.55-1.43 (m, 2H), 0.99 (t, 3H, J=7.3 Hz). MS (APCI) m/z 387 [M+H]+.

Workup

  1. filtrationThe crude mixture is filtered through a silica pad
  2. customAfter purification on silica eluting with 25% EtOAc in hexane

Sources & evidence

ORD record
ord-8c5f9f26391b4cc090ac97813fa6ecab
Source dataset
uspto-grants-2008_04
Patent number
US07365068B2

Reaction notes

Loading…