Methane → HCID 178446833, compound

HRID 358263Notes

Reaction equation

HRID 358263 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[C:13]([N+]#[C-])(C)([CH3:15])[CH3:14].N1[CH:23]=[CH:22][N:21]=C1.Cl.[OH-].[Na+].C>C(OCC)(=O)C>[CH2:23]([C:22]([NH2:21])=[N:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[CH:10][NH:11][CH:12]=2)=[CH:6][CH:7]=1)[CH2:14][CH2:13][CH3:15]

Participants

8

Reactant 6

HCID 297MethaneHCID 313Hydrochloric AcidHCID 795ImidazoleHCID 14798Sodium HydroxideHCID 23577Tert-Butyl isocyanideHCID 178507418HCID 178507418, compound

Product 1

HCID 178446833HCID 178446833, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.3 gm of 4-(p-aminophenyl)-1-H-imidazole, 1.25 gm of t-butylisonitrile, 0.2 gm of AgCl, and 0.11 gm of imidazole was heated at 100° C. for 13 hours. The thick reaction mixture was treated with 10% HCl and ethyl acetate. The acid solution was adjusted to pH 6.5 with 10% NaOH, treated with charcoal, filtered, and adjusted to an alkaline pH. The layer which separated was extracted with ethyl acetate. After drying, the organic solution was evaporated to dryness to yield 0.38 gm of the desired compound.

Workup

  1. filtrationfiltered
  2. customThe layer which separated
  3. extractionwas extracted with ethyl acetate
  4. customAfter drying
  5. customthe organic solution was evaporated to dryness

Sources & evidence

ORD record
ord-edef0fb393f741b0a457f8f86d72337d
Source dataset
uspto-grants-1984_08
Patent number
US04465841

Reaction notes

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