Isopropylamine → N-Ethoxycarbonyl-N'-isopropylthiourea

HRID 637258Notes

Reaction equation

HRID 637258 reaction equation
[CH:1]([NH2:4])([CH3:3])[CH3:2].[CH2:5]([O:7][C:8]([N:10]=[C:11]=[S:12])=[O:9])[CH3:6]>C(OCC)C>[CH2:5]([O:7][C:8]([NH:10][C:11]([NH:4][CH:1]([CH3:3])[CH3:2])=[S:12])=[O:9])[CH3:6]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 85320Ethyl isothiocyanatoformate

Product 1

HCID 3037300N-Ethoxycarbonyl-N'-isopropylthiourea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 7.1 grams of isopropylamine in 40 ml of anhydrous ethyl ether was added dropwise in 30 minutes with stirring to a solution of 15.5 grams of ethoxycarbonyl isothiocyanate (Preparation 1) in 10 ml of anhydrous ethyl ether. The reaction vessel was cooled with an ice-water bath. The reaction mixture was let stand at an ambient room temperature. After the reaction was complete, the solution was concentrated by stripping off most of the solvent under reduced pressure. The crystals were collected by filtering and washing with hexanes. The first crop weighed 8.1 grams, m.p. 52.5°-54° C. The second crop weighed 7 grams, m.p. 52°-54° C.

Workup

  1. temperatureThe reaction vessel was cooled with an ice-water bath
  2. customat an ambient room temperature
  3. concentrationthe solution was concentrated
  4. customThe crystals were collected
  5. filtrationby filtering
  6. washwashing with hexanes

Sources & evidence

ORD record
ord-5a6e6511a0d04be0bb2b206ce8ffaa56
Source dataset
uspto-grants-1985_12
Patent number
US04556482

Reaction notes

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