Triethylamine → 3-Ethyl-5-[5,5-dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]rhodanine

HRID 1283834Notes

Reaction equation

HRID 1283834 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]([N:22]1[C:26](=[O:27])[CH2:25][S:24][C:23]1=[S:28])[CH3:21].C(N(CC)CC)C>C(O)C>[CH2:20]([N:22]1[C:26](=[O:27])[C:25](=[C:7]2[CH2:12][C:11]([CH3:14])([CH3:13])[CH2:10][C:9]([N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:8]2)[S:24][C:23]1=[S:28])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 820983-EthylrhodanineHCID 21516721N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate

Product 1

HCID 737950553-Ethyl-5-[5,5-dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]rhodanine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate (3.1 g., 0.01 mol.), 3-ethylrhodanine (1.6 g., 0.011 mol.) and triethylamine (3.1 ml.) are dissolved in ethanol (20 ml.) and heated at reflux for 10 minutes. After chilling, the solid is collected on a filter, rinsed with ethanol and dried. After one recrystallization from pyridine/methanol, the yield of purified dye is 2.2 g. (65%), m.p. 234°-235°C. with decomposition. This dye is an excellent spectral sensitizer for photographic silver halide emulsions in the minus blue region of the spectrum as set forth in Table 2 hereinafter.

Workup

  1. temperatureheated
  2. temperatureat reflux for 10 minutes
  3. temperatureAfter chilling
  4. customthe solid is collected on a filter
  5. washrinsed with ethanol
  6. customdried
  7. customAfter one recrystallization from pyridine/methanol

Sources & evidence

ORD record
ord-4ae5b00128a3440da8312bdc0aa957d1
Source dataset
uspto-grants-1976_08
Patent number
US03976661

Reaction notes

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