Sodium Chloride → HCID 13209336, compound

HRID 614518Notes

Reaction equation

HRID 614518 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:16])[C:11]=1[NH:12][C:13](=[O:15])[NH2:14])[CH:5]([OH:8])[CH2:6]Br.[C:17]([NH2:21])([CH3:20])([CH3:19])[CH3:18].C(=O)([O-])[O-].[Na+].[Na+].[Cl-].[Na+]>O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([Cl:16])[C:11]=1[NH:12][C:13](=[O:15])[NH:14][C:4]([CH3:9])([CH3:5])[CH3:3])[CH:5]([OH:8])[CH2:6][NH:21][C:17]([CH3:20])([CH3:19])[CH3:18]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6385Tert-ButylamineHCID 10340Sodium CarbonateHCID 54001236HCID 54001236, compound

Product 1

HCID 13209336HCID 13209336, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.86 g. of 3,5-dichloro-4-carbamoylamino-αbromomethylbenzyl alcohol and 10 ml. of tert-butylamine was heated to 90°-100° C. for 2 days in a sealed tube. After cooling the reaction mixture, the solvent was distilled off under reduced pressure and after adding to the residue formed 50 ml. of ethyl acetate, 50 ml. of water, and an excessive amount of sodium carbonate followed by stirring for 30 minutes, sodium chloride was added to the mixture until the mixture was saturated. Then, the mixture was separated into an ethyl acetate layer and an aqueous layer. The ethyl acetate layer formed was washed with a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. Then, after filtering, the solvent was distilled off from the filtrate under reduced pressure. By recrystallizing the residue from ethyl acetate, 0.24 g. of 3,5-dichloro-4-tert-butylcarbamoylamino-α-(tert-butylaminomethyl)benzyl alcohol having a melting point of 167°-169° C. was obtained.

Workup

  1. additionA mixture of 0.86 g
  2. temperatureAfter cooling the reaction mixture
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionafter adding to the residue
  5. customformed 50 ml
  6. customThen, the mixture was separated into an ethyl acetate layer
  7. customThe ethyl acetate layer formed
  8. washwas washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. filtrationThen, after filtering
  11. distillationthe solvent was distilled off from the filtrate under reduced pressure
  12. customBy recrystallizing the residue from ethyl acetate, 0.24 g

Sources & evidence

ORD record
ord-a3b1fbb970ba44afa948bbbf061ff4fa
Source dataset
uspto-grants-1979_03
Patent number
US04145363

Reaction notes

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