Triethylamine → 1,3-Diethyl-5-[5,5-dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]-2-thiobarbituric acid

HRID 1283835Notes

Reaction equation

HRID 1283835 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:29](=[O:30])[CH2:28][C:26](=[O:27])[N:25]([CH2:31][CH3:32])[C:23]1=[S:24])[CH3:21].C(N(CC)CC)C>C(O)C>[CH2:31]([N:25]1[C:26](=[O:27])[C:28](=[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)[C:29](=[O:30])[N:22]([CH2:20][CH3:21])[C:23]1=[S:24])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 788901,3-Diethyl-2-thiobarbituric acidHCID 21516721N-(3-Chloro-5,5-dimethylcyclohex-2-en-1-ylidene)-pyrrolidinium perchlorate

Product 1

HCID 215167331,3-Diethyl-5-[5,5-dimethyl-1-(1-pyrrolidinyl)-1-cyclohexen-3-ylidene]-2-thiobarbituric acid

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.), 1,3-diethyl-2-thiobarbituric acid (2.0 g., 0.091 mol.) and triethylamine (3.1 ml.) are dissolved in ethanol (15 ml.) and heated at reflux for 10 minutes. After chilling, the crude dye is collected on a filter, rinsed with ethanol and dried. After one recrystallization from methanol, the yield of purified dye is 2.3 g. (64%), m.p. 226°-227°C. This dye is an excellent spectral sensitizer for photographic silver halide emulsions as shown in Table 2 hereinafter.

Workup

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

Sources & evidence

ORD record
ord-5a6ff00a0812419e8ac610a1459fe236
Source dataset
uspto-grants-1976_08
Patent number
US03976661

Reaction notes

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