Hydrochloric Acid → HCID 22163914, compound

HRID 1087798Notes

Reaction equation

HRID 1087798 reaction equation
[OH:1][NH:2][CH:3]([C:5]1[CH:9]=[CH:8][N:7]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[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:9]=[CH:8][N:7]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:17])[CH:6]=1)[CH3:4])[OH:1])(=[O:20])[NH2:24]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6371PhosgeneHCID 14923Ammonium HydroxideHCID 54283156HCID 54283156, compound

Product 1

HCID 22163914HCID 22163914, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

A solution of 1.0 g of N-hydroxy-1-[1-(2,6-dimethylphenyl)-1H-pyrrol-3-yl]-ethylamine in 60 ml of toluene is stirred and treated first with one mole equivalent of 4.0M ethanolic HCl, followed by 10 ml of 2.0M 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 to yield N-carbamoyl-N-hydroxy-1-[1-(2,6-dimethylphenyl)-1H-pyrrol-3-yl]-ethylamine.

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

Sources & evidence

ORD record
ord-87ca2e9fa3de44bd90db5dba12724d6f
Source dataset
uspto-grants-1990_10
Patent number
US04960787

Reaction notes

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