Dichloromethane → 62780-15-8

HRID 27839Notes

Reaction equation

HRID 27839 reaction equation
C(Cl)Cl.[Cl:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:6]=1[CH:12](O)[CH2:13][NH:14][C:15]([NH:21]C(OC)=O)=[N:16][C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C.S(Cl)(C)(=O)=O>CO>[CH3:20][O:19][C:17]([NH:16][C:15]1[NH:21][CH:12]([C:6]2[C:5]([Cl:4])=[CH:10][CH:9]=[CH:8][C:7]=2[Cl:11])[CH2:13][N:14]=1)=[O:18]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178502520HCID 178502520, compound

Product 1

HCID 17387562780-15-8Yield 92.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

To 5 l of a methylene chloride solution containing 550 g of 1-(2',6'-dichlorophenyl)-2-(2',3'-bis-methoxycarbonylguanidino) ethanol was added 530 ml of triethylamine. The mixture was stirred until a clear solution formed. Mesyl chloride, 160 ml was then added dropwise with stirring at such a rate that the solution temperature did not pass 35° C. The reaction was complete after 30 minutes. One liter of methanol was added to the reaction mass and the resulting mixture filtered. To the filtrate was added 4 l of methanol and a solution of 270 g of sodium hydroxide in 550 ml of deionized water. The mixture was vigorously agitated and heated to about 40° C. for one hour. The reaction solution was then vacuum distilled until approximately 5 l of distillate had been collected. After addition of 8 l of deionized water to the distillation flask, vacuum distillation was continued, collecting 3 l of distillate. The pot residue was cooled to about 20° C. and stirred for about 1 hour. The imidazole product precipitated from the residual reaction solution and was filtered, washed with 3 l of deionized water then 1 liter of methanol. Drying at 65° C. in a vacuum oven gave 403 g of 4,5-dihydro-2-methoxycarbonylamino-5-(2',6'-dichlorophenyl)imidazole, m.p. 231°-232° C. (dec.).

Workup

  1. customformed
  2. stirringwith stirring at such a rate that the solution temperature
  3. customdid not pass 35° C
  4. filtrationthe resulting mixture filtered
  5. additionTo the filtrate was added 4 l of methanol
  6. stirringThe mixture was vigorously agitated
  7. distillationvacuum distilled until approximately 5 l of distillate
  8. customhad been collected
  9. additionAfter addition of 8 l of deionized water
  10. distillationto the distillation flask, vacuum distillation
  11. distillationcollecting 3 l of distillate
  12. temperatureThe pot residue was cooled to about 20° C.
  13. stirringstirred for about 1 hour
  14. customThe imidazole product precipitated from the residual reaction solution
  15. filtrationwas filtered
  16. washwashed with 3 l of deionized water
  17. customDrying at 65° C. in a vacuum oven

Sources & evidence

ORD record
ord-7602f609d8bb4ba18189eece3d658ede
Source dataset
uspto-grants-1980_09
Patent number
US04224224

Reaction notes

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