Isopropylamine → phenyl N-isopropylcarbamate

HRID 1112604Notes

Reaction equation

HRID 1112604 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].Cl[C:6]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7].[OH-].[Na+]>C(Cl)Cl>[CH:1]([NH:4][C:6](=[O:7])[O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6363IsopropylamineHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformate

Product 1

HCID 302841phenyl N-isopropylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same procedure as in Example 4, isopropylamine (2.36g, 0.04 mole) was reacted with phenyl chloroformate (6.0g, 0.038 mole) in methylene chloride (35 ml) and with aqueous sodium hydroxide. The reaction mixture was stirred for two hours, then allowed to separate. The organic layer was dried over anhydrous magnesium sulfate, then gravity filtered. The filtrate was stripped of solvent on the Rotovap, leaving pure white crystals weighing 6.66g, MP 81°-82° C.

Workup

  1. customto separate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationgravity filtered
  4. customleaving pure white crystals

Sources & evidence

ORD record
ord-5846d3de58b642efa883350bc09d94be
Source dataset
uspto-grants-1978_10
Patent number
US04123450

Reaction notes

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