Methanol → 62780-15-8

HRID 27840Notes

Reaction equation

HRID 27840 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9](O)[CH2:10][NH:11][C:12]([NH:18]C(OC)=O)=[N:13][C:14]([O:16][CH3:17])=[O:15].S(Cl)(Cl)=O.CO.[OH-].[Na+]>C(Cl)Cl.O>[CH3:17][O:16][C:14]([NH:13][C:12]1[NH:18][CH:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[CH2:10][N:11]=1)=[O:15]

Participants

7

Reactant 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 178502520HCID 178502520, compound

Product 1

HCID 17387562780-15-8

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To 1 gram of 1-(2',6'-dichlorophenyl)-2-(2',3'-bismethoxycarbonylguanidino) ethanol dissolved in 20 ml of methylene chloride was added dropwise with cooling at 0° C. 0.35 g of thionyl chloride. At the conclusion of the addition period, the solution was stirred for an additional 60 minutes at room temperature. After the addition of 20 ml of methyl alcohol, a solution of 0.5 g of sodium hydroxide in 2 ml of water was added and the resulting mixture refluxed for 60 minutes. The reaction solution was evaporated to low volume under vacuum and 50 ml of water added. The precipitated solid was collected, washed with methanol, followed by water and dried. 4,5-Dihydro-2-methoxycarbonylamino-5-(2',6'-dichlorophenyl)imidazole was isolated, 0.3 g, m.p. 229-230 (dec.).

Workup

  1. additionwas added dropwise
  2. additionAt the conclusion of the addition period
  3. temperaturethe resulting mixture refluxed for 60 minutes
  4. customThe reaction solution was evaporated to low volume under vacuum and 50 ml of water
  5. additionadded
  6. customThe precipitated solid was collected
  7. washwashed with methanol
  8. customdried

Sources & evidence

ORD record
ord-fe32208c60404b3d8bafaaa59d7f9daa
Source dataset
uspto-grants-1980_09
Patent number
US04224224

Reaction notes

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