Methyl chloroformate → HCID 20222097, compound

HRID 980147Notes

Reaction equation

HRID 980147 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[NH2:6][C:7]1[CH:20]=[CH:19][C:10]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:9][CH:8]=1>C(Cl)(Cl)Cl>[CH3:5][O:4][C:2]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([O:11][CH2:12][CH2:13][N:14]2[CH:18]=[CH:17][N:16]=[CH:15]2)=[CH:19][CH:20]=1)=[O:3]

Participants

4

Reactant 2

HCID 6586Methyl chloroformateHCID 135692034-[2-(1H-Imidazol-1-yl)ethoxy]aniline

Product 1

HCID 20222097HCID 20222097, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Methyl chloroformate (0.5 g) was added to a stirred solution of 1-[2-(4-aminophenoxy)ethyl]imidazole (1.0 g) in chloroform (50 ml) and the mixture was stirred at room temperature for 2 hours and then evaporated. The residue was dissolved in water and made basic by the addition of sodium bicarbonate. The resulting precipitate was filtered off, washed with water and crystallised from methanol/water to give 1-[2-(4-methoxycarbonylaminophenoxy)ethyl]imidazole (1.13 g), m.p. 152°-153° C. Found: C, 59.77; H, 5.81; N, 15.92. C13H15N3O3 requires: C, 59.76; H, 5.79; N, 16.08%.

Workup

  1. customevaporated
  2. dissolutionThe residue was dissolved in water
  3. additionmade basic by the addition of sodium bicarbonate
  4. filtrationThe resulting precipitate was filtered off
  5. washwashed with water
  6. customcrystallised from methanol/water

Sources & evidence

ORD record
ord-40897fae29fd4e65929333317c4f2f2f
Source dataset
uspto-grants-1987_01
Patent number
US04636500

Reaction notes

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