Ammonia → HCID 70504694, compound

HRID 1389515Notes

Reaction equation

HRID 1389515 reaction equation
BrBr.C(OC(NC1C(Br)=CC(C(=O)C)=CC=1C)=O)C.Br.C(OC(NC1C(Br)=CC(C(=O)CBr)=CC=1C)=O)C.C(N)(C)(C)C.[CH2:44]([O:46][C:47]([NH:49][C:50]1[C:55]([Br:56])=[CH:54][C:53]([C:57](=[O:64])[CH2:58][NH:59][C:60]([CH3:63])([CH3:62])[CH3:61])=[CH:52][C:51]=1[CH3:65])=[O:48])[CH3:45].N.[ClH:67]>C(Cl)(Cl)Cl.O>[ClH:67].[CH2:44]([O:46][C:47]([NH:49][C:50]1[C:55]([Br:56])=[CH:54][C:53]([CH:57]([OH:64])[CH2:58][NH:59][C:60]([CH3:62])([CH3:61])[CH3:63])=[CH:52][C:51]=1[CH3:65])=[O:48])[CH3:45]

Participants

11

Reactant 8

HCID 222AmmoniaHCID 260Hydrogen BromideHCID 313Hydrochloric AcidHCID 6385Tert-ButylamineHCID 24408BromineHCID 20296719HCID 20296719, compoundHCID 70564103HCID 70564103, compoundHCID 86737433HCID 86737433, compound

Product 1

HCID 70504694HCID 70504694, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

6.5 gm of bromine were added dropwise into a boiling solution of 12 gm of 4'-ethoxycarbonylamino-5'-bromo-3'-methyl-acetophenone in 200 ml of chloroform, whereupon hydrobromic acid was rapidly formed. The solution obtained, containing 4'-ethoxycarbonylamino-5', 2-dibromo-3'-methyl-acetophenone, was admixed with 14.6 gm of tert. butylamine. After refluxing for 30 minutes, the resulting solution containing 4'-ethoxycarbonylamino-5'-bromo-3'-methyl-2-tert. butylamino-acetophenone was evaporated in vacuo. The residue was dissolved in 50 ml of methanol and 20 ml of water. Reduction was effected by addition thereto of a solution of 3.8 gm of sodium borohydride in 20 ml of water with simultaneous adjustment of the pH to between 6 and 8 by addition of dilute hydrochloric acid. After reduction was complete, the methanol was distilled off in vacuo. The residue obtained was admixed with water, and the resulting solution was made alkaline by addition of liquid ammonia and extracted with chloroform. The organic phase was separated, dried and evaporated in vacuo. The evaporation residue was purified on a silicagel column (eluant: chloroform/methanol 2:1). After evaporation, the residue was dissolved in ethanol, and the solution obtained was admixed with ethereal hydrochloric acid to yield 1-(4-ethoxycarbonylamino-5-bromo-3-methyl-phenyl)-2-tert. butylamino-ethanol hydrochloride.

Workup

  1. customwas rapidly formed
  2. customThe solution obtained
  3. temperatureAfter refluxing for 30 minutes
  4. customwas evaporated in vacuo
  5. dissolutionThe residue was dissolved in 50 ml of methanol
  6. additionReduction was effected by addition
  7. additionof a solution of 3.8 gm of sodium borohydride in 20 ml of water with simultaneous adjustment of the pH to between 6 and 8 by addition of dilute hydrochloric acid
  8. distillationthe methanol was distilled off in vacuo
  9. customThe residue obtained
  10. extractionextracted with chloroform
  11. customThe organic phase was separated
  12. customdried
  13. customevaporated in vacuo
  14. customThe evaporation residue was purified on a silicagel column (eluant: chloroform/methanol 2:1)
  15. customAfter evaporation
  16. dissolutionthe residue was dissolved in ethanol
  17. customthe solution obtained

Sources & evidence

ORD record
ord-ef5fda9357ca4066bee75092d2f334bc
Source dataset
uspto-grants-1981_01
Patent number
US04244967

Reaction notes

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