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

HRID 1283837Notes

Reaction equation

HRID 1283837 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.[CH2:20]([S:32]([CH2:35][C:36]#[N:37])(=[O:34])=[O:33])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31].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:35]([S:32]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])(=[O:34])=[O:33])[C:36]#[N:37])[CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 104334(Dodecylsulphonyl)acetonitrileHCID 21516721N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate

Product 1

HCID 53637640[5,5-Dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]-(dodecylsulfonyl)acetonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate (3.2 g.), dodecylsulfonylacetonitrile (2.7 g.) and triethylamine (3.1 ml.) are dissolved in ethanol (15 ml.) and heated at reflux for 5 minutes. After chilling, the solid is collected on a filter, washed with methanol and dried. Obtaining pure dye by recrystallization from methanol proved difficult. The product is eluted from basic alumina, using a 10% methanol-90% chloroform solvent mixture, and then recrystallized from methanol. The yield of purified dye is 0.5 g. (11%), m.p. 114°-115°C. This dye compound shows good ultraviolet absorption characteristics as indicated in the data in Table 1 below.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 minutes
  3. temperatureAfter chilling
  4. customthe solid is collected on a filter
  5. washwashed with methanol
  6. customdried
  7. customObtaining pure dye
  8. customby recrystallization from methanol proved difficult
  9. washThe product is eluted from basic alumina
  10. customrecrystallized from methanol
  11. customultraviolet absorption characteristics

Sources & evidence

ORD record
ord-86596acdeb1f4ef388dba2a992ce8665
Source dataset
uspto-grants-1976_08
Patent number
US03976661

Reaction notes

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