1-Isocyanato-4-methoxybenzene → HCID 86753485, compound

HRID 1459679Notes

Reaction equation

HRID 1459679 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][CH2:11][CH2:12][CH3:13])=[C:7]([C:14](=[O:30])[C:15]3[CH:20]=[C:19]([I:21])[C:18]([CH2:22][CH3:23])=[C:17]([I:24])[C:16]=3[O:25][CH2:26][C:27]([OH:29])=[O:28])[C:6]=2[CH:31]=1.[CH3:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([N:40]=[C:41]=[O:42])=[CH:36][CH:35]=1>C1COCC1>[CH2:10]([C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:41]([NH:40][C:37]3[CH:38]=[CH:39][C:34]([O:33][CH3:32])=[CH:35][CH:36]=3)=[O:42])=[CH:31][C:6]=2[C:7]=1[C:14](=[O:30])[C:15]1[CH:20]=[C:19]([I:21])[C:18]([CH2:22][CH3:23])=[C:17]([I:24])[C:16]=1[O:25][CH2:26][C:27]([OH:29])=[O:28])[CH2:11][CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 794431-Isocyanato-4-methoxybenzeneHCID 54224308HCID 54224308, compound

Product 1

HCID 86753485HCID 86753485, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-amino-2-n-butyl-3-(3,5-diiodo-4-ethylcarboxymethoxybenzoyl)-benzofuran (prepared as in Example 1(g), 320 mg, 0.5 mmol) and p-methoxyphenylisocyanate (75 mg, 0.5 mmol) in THF (10 mL) was stirred at room temperature for 3 h. The mixture was concentrated, ethyacetate was added and the organic layer was washed with water, 1M HCl, then NaHCO3 (sat) then brine, dried using MgSO2 and then concentrated. Purification by column chromathography on silica with a 95:5 mixture of methylenechloride--methanol as eluant produced 300 mg (75%) of 2-n-butyl-3-(3,5-diiodo-4-ethyl carboxymethoxybenzoyl)-5-(4-methoxyphenylureido)benzofuran.

Workup

  1. concentrationThe mixture was concentrated
  2. additionethyacetate was added
  3. washthe organic layer was washed with water, 1M HCl
  4. dry with materialNaHCO3 (sat) then brine, dried
  5. concentrationconcentrated
  6. customPurification by column chromathography on silica
  7. additionwith a 95:5 mixture of methylenechloride

Sources & evidence

ORD record
ord-1eeacd5d377d4384a98642713bc543e4
Source dataset
uspto-grants-1998_12
Patent number
US05854282

Reaction notes

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