Benzene, 1-ethoxy-4-isocyanato- → HCID 66919725, compound

HRID 523869Notes

Reaction equation

HRID 523869 reaction equation
O.[ClH:2].Cl.[NH:4]1[CH2:8][CH2:7][N:6]=[C:5]1[C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].[CH2:16]([O:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]=[C:26]=[O:27])=[CH:21][CH:20]=1)[CH3:17]>CN(C)C=O>[ClH:2].[NH:6]1[CH2:7][CH2:8][N:4]=[C:5]1[C:9]1[CH:10]=[C:11]([NH:12][C:26]([NH:25][C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:16][CH3:17])=[CH:20][CH:21]=2)=[O:27])[CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 122887Benzene, 1-ethoxy-4-isocyanato-HCID 441194253-(4,5-Dihydro-1H-imidazol-2-yl)aniline--hydrogen chloride--water (1/2/1)

Product 1

HCID 66919725HCID 66919725, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(4,5-dihydro-1H-imidazol-2-yl) aniline dihydrochloride monohydrate (stored with 4 A molecular sieves, 48 mg, 0.19 mmol) and 4-ethoxyphenyl isocyanate (33 mg, 0.20 mmol) in dimethylformamide (2 ml) was stirred at room temperature overnight. After removal of the solvent, water (2 ml) was added and the resulting precipitate was collected (18 mg, 64% yield) by filtration. 1H NMR (600 MHz, DMSO-d6) δ 10.5 (br s, 1H), 9.12 (br s, 1H), 8.11 (s, 1H), 7.68 (d, 1H, J=8.4 Hz), 7.52 (t, 1H, 8.4 Hz), 7.47 (d, 1H, J=7.2 Hz), 7.35 (d, 2H, J=7.2 Hz), 6.86 (d, 2H, J=7.2 Hz), 3.98 (s, 4H). MS: m/z Calcd 324.4 Found MH+ 325.5

Workup

  1. customAfter removal of the solvent, water (2 ml)
  2. additionwas added
  3. customthe resulting precipitate was collected (18 mg, 64% yield)
  4. filtrationby filtration

Sources & evidence

ORD record
ord-91129398df3b4086ba0f3023f6f700fe
Source dataset
uspto-grants-2016_05
Patent number
US09340505B2

Reaction notes

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