Aniline → HCID 12511413, compound

HRID 1283422Notes

Reaction equation

HRID 1283422 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:9]([N:11]1[CH2:15][CH2:14][NH:13][C:12]1=[O:16])=[O:10].C(N(CC)CC)C>O1CCCC1.O>[C:2]1([NH:1][C:9]([N:11]2[CH2:15][CH2:14][NH:13][C:12]2=[O:16])=[O:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 832412-Oxoimidazolidine-1-carbonyl chloride

Product 1

HCID 12511413HCID 12511413, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

10.2 parts by weight of aniline were first introduced into 120 parts by volume of 80% strength aqueous tetrahydrofurane at pH = 8 and 14.9 parts by weight of N-chlorocarbonyl-imidazolid-2-one were added in portions at room temperature while stirring and keeping the pH value at 7-8 by simultaneous addition of triethylamine. The mixture was further stirred until the pH was constant, 80 parts by volume of water were added, the tetrahydrofurane was stripped off in vacuo, the pH was adjusted to 2.5 and after standing for one hour in an ice bath the product which had precipitated was filtered off. It was washed with ice water and dried over P2O5 in a vacuum desiccator.

Workup

  1. additionwere added in portions at room temperature
  2. stirringThe mixture was further stirred until the pH
  3. customthe product which had precipitated
  4. filtrationwas filtered off
  5. washIt was washed with ice water
  6. dry with materialdried over P2O5 in a vacuum desiccator

Sources & evidence

ORD record
ord-96e8734e515f42be9a2194e34739be16
Source dataset
uspto-grants-1976_08
Patent number
US03975375

Reaction notes

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