4-Chlorophenyl Isocyanate → HCID 69202950, compound

HRID 2221452Notes

Reaction equation

HRID 2221452 reaction equation
Cl.[NH2:2][CH2:3][C:4]#[C:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]=[C:24]=[O:25])=[CH:19][CH:18]=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:25])[NH:2][CH2:3][C:4]#[C:5][C:6]2[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=2)=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 76934-Chlorophenyl IsocyanateHCID 8471TriethylamineHCID 69202155847460-43-9

Product 1

HCID 69202950HCID 69202950, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 4-(3-aminoprop-1-ynyl)benzoate hydrochloride (see Example 1, Steps 1-3 above; 150 mg, 0.66 mmol) in THF (5 ml) was added 4-chlorophenyl isocyanate (102 mg, 0.66 mmol) and triethylamine (278 μL, 2.0 mmol). The reaction mixture was stirred for 30 min, diluted with ethyl acetate (50 ml), and sequentially washed with water (25 ml), 0.5M aqueous HCl (25 ml), saturated sodium bicarbonate (25 ml), and finally with brine (25 ml). The organic phase was dried over sodium sulfate and concentrated in vacuo to provide methyl 4-[3-(3-(4-chlorophenyl)-ureido)prop-1-ynyl]-benzoate as a white solid.

Workup

  1. washsequentially washed with water (25 ml), 0.5M aqueous HCl (25 ml), saturated sodium bicarbonate (25 ml)
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f8396547e26496d891b3d2e124cc55e
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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