Hydrochloric Acid → HCID 19905461, compound

HRID 2371965Notes

Reaction equation

HRID 2371965 reaction equation
[OH:1][NH:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:7][CH:6]=1)[CH3:4].Cl.[C:19](Cl)(Cl)=[O:20].[OH-].[NH4+:24]>C1(C)C=CC=CC=1.O>[C:19]([N:2]([CH:3]([C:5]1[CH:6]=[CH:7][C:8]([N:11]2[C:15]([CH3:16])=[CH:14][CH:13]=[C:12]2[CH3:17])=[CH:9][CH:10]=1)[CH3:4])[OH:1])(=[O:20])[NH2:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 14923Ammonium HydroxideHCID 54097870HCID 54097870, compound

Product 1

HCID 19905461HCID 19905461, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 1.4 g of N-hydroxy-1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-ethylamine in 60 ml of toluene is stirred and treated first with one mole equivalent of 4.0 M ethanolic HCl, followed by 15 ml of 2.0 M phosgene in toluene. The solution is stirred for 7 hours, 50 ml of concentrated ammonium hydroxide is added and the mixture is stirred overnight. Excess water is then added and the mixture is again stirred for 2 hours. The organic layer is separated, washed with brine, dried over magnesium sulfate, treated with charcoal and evaporated to dryness. The residue is crystallized from ether to yield N-carbamoyl-N-hydroxy-1-[4-(2,5-dimethyl-1H-pyrrol-1-yl)-phenyl]-ethyl-amine;

Workup

  1. stirringthe mixture is stirred overnight
  2. stirringthe mixture is again stirred for 2 hours
  3. customThe organic layer is separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with charcoal
  7. customevaporated to dryness
  8. customThe residue is crystallized from ether

Sources & evidence

ORD record
ord-3bc4e23f7ac5487bbe228f10269ae05d
Source dataset
uspto-grants-1992_03
Patent number
US05096919

Reaction notes

Loading…