Triethylamine → [5,5-Dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]-(methylsulfonyl)acetonitrile

HRID 1283836Notes

Reaction equation

HRID 1283836 reaction equation
Cl([O-])(=O)(=O)=O.Cl[C:7]1[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9](=[N+:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:8]=1.[CH3:20][S:21]([CH2:24][C:25]#[N:26])(=[O:23])=[O:22].C(N(CC)CC)C>C(O)C>[CH3:13][C:11]1([CH3:14])[CH2:10][C:9]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[CH:8][C:7](=[C:24]([S:21]([CH3:20])(=[O:23])=[O:22])[C:25]#[N:26])[CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75283(Methylsulfonyl)acetonitrileHCID 21516721N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate

Product 1

HCID 54397242[5,5-Dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]-(methylsulfonyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate (4.7 g., 0.015 mol.), methylsulfonylacetonitrile (1.8 g., 0.015 mol.) and triethylamine (4.6 ml.) are dissolved in ethanol (15 ml.) and heated at reflux for 5 minutes. After chilling, the crude dye is collected on a filter, washed with methanol and dried. After one recrystallization from pyridine/methanol, the yield of purified dye is 1.2 g. (27%), m.p. 260°-261°C. with decomposition. The above dye compound has excellent absorption characteristics in the ultraviolet region of the spectrum as shown in Table 1 below.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 minutes
  3. temperatureAfter chilling
  4. customthe crude dye is collected on a filter
  5. washwashed with methanol
  6. customdried
  7. customAfter one recrystallization from pyridine/methanol
  8. customabsorption characteristics in the ultraviolet region of the spectrum

Sources & evidence

ORD record
ord-eb7fddd2d6dc4b318dc3f49420317052
Source dataset
uspto-grants-1976_08
Patent number
US03976661

Reaction notes

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