6-Amino-3-butyl-phthalide → 3-Butyl-6-ureido-phthalide

HRID 2120188Notes

Reaction equation

HRID 2120188 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]([CH2:12][CH2:13][CH2:14][CH3:15])[O:7][C:8]2=[O:9])=[CH:4][CH:3]=1.[O-:16][C:17]#[N:18].[K+]>C(O)(=O)C.O>[CH2:12]([CH:6]1[C:5]2[C:10](=[CH:11][C:2]([NH:1][C:17]([NH2:18])=[O:16])=[CH:3][CH:4]=2)[C:8](=[O:9])[O:7]1)[CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 2

HCID 98777066-Amino-3-butyl-phthalideHCID 11378442Potassium cyanate2×

Product 1

HCID 234391203-Butyl-6-ureido-phthalide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent3×

Conditions

Temperature
55 °C

Procedure

To a solution of 8.27 g (0.04 mol) of the compound obtained in Example 4 in 39.4 ml of glacial acetic acid there are added, with sting, 25 ml of water, and to this solution there is slowly added a solution of 6.54 g of potassium cyanate in 10 ml of water. Once a white precipitate appears, the remaining potassium cyanate solution is added in one portion immediately. The mixture is warmed at 55° C., and stirred for 1 hour, then put aside at room temperature for 3 hours. 50 ml of water are added and the mixture is cooled to 5° C.; the separated solid is collected and dissolved in 10% sodium carbonate solution. Any insoluble material is filtered off and the filtrate is acidified with dilute sulphuric acid. The solid is collected and washed with water and dried, giving the title compound.

Workup

  1. waitput aside at room temperature for 3 hours
  2. temperaturethe mixture is cooled to 5° C.
  3. customthe separated solid is collected
  4. dissolutiondissolved in 10% sodium carbonate solution
  5. filtrationAny insoluble material is filtered off
  6. customThe solid is collected
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-42ca336bca1c4b0db50b5b1739f07814
Source dataset
uspto-grants-2004_02
Patent number
US06689808B2

Reaction notes

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