Sodium hydride → HCID 67919987, compound

HRID 1091203Notes

Reaction equation

HRID 1091203 reaction equation
[H-].[Na+].[C:3]([CH2:6][C:7](=[O:9])[CH3:8])(=[O:5])[CH3:4].[CH2:10]([N:14]([CH2:58][CH2:59][CH2:60][CH3:61])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)(O)[CH:22]=[CH:23][CH:24]=[C:25]([C:34]2[CH:39]=[CH:38][C:37]([N:40]([CH2:45][CH2:46][CH2:47][CH3:48])[CH2:41][CH2:42][CH2:43][CH3:44])=[CH:36][CH:35]=2)[C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:17][CH:16]=1)[CH2:11][CH2:12][CH3:13].Cl([O-])(=O)(=O)=O>CN(C)C=O>[CH2:45]([N:40]([CH2:41][CH2:42][CH2:43][CH3:44])[C:37]1[CH:36]=[CH:35][C:34]([C:25]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[CH:24][CH2:23][CH:22]=[C:21]([C:18]2[CH:17]=[CH:16][C:15]([N:14]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:58][CH2:59][CH2:60][CH3:61])=[CH:20][CH:19]=2)[C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][CH:51]=2)=[CH:39][CH:38]=1)[CH2:46][CH2:47][CH3:48].[C:3]([CH2:6][C:7](=[O:9])[CH3:8])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 31261AcetylacetoneHCID 131717162HCID 131717162, compound

Product 1

HCID 67919987HCID 67919987, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.2 g of a 60% sodium hydride was dispersed in 200 ml of well-dried N,N-dimethylformamide (DMF) in a 300-ml. Erlenmeyer flask. To this dispersion, 3.00 g of acetylacetone was slowly added at room temperature and the mixture was stirred for 1 hour. To this mixture, 15.71 g of 1,5-bis-(p-di-n-butylaminophenyl)-1,5-bis-(p-methoxyphenyl)-2,4-pentadiene-1-ol-perchlorate prepared in Synthesis Example 2,5 was slowly added. This reaction mixture was stirred at room temperature for 1 hour. Then the reaction mixture was poured into 1 l of ice water. As a result, solids separated from the reaction mixture. The solids were washed with water and dried under reduced pressure. After the completion of drying, the solids were subjected to column chromatography, so that 10.0 g of 1,5-bis-(p-di-n-butylaminophenyl)-1,5-bis-(p-methoxyphenyl)-1,4-pentadiene-3-acetylacetone (Leuco Dye No. 26 ) according to the present invention was obtained in the form of light yellow viscous material. The yield was 63.7%. The characteristics absorption bands in the infrared spectrum of the thus obtained product were as follows:

Workup

  1. additionwas slowly added
  2. stirringThis reaction mixture was stirred at room temperature for 1 hour
  3. customAs a result, solids separated from the reaction mixture
  4. washThe solids were washed with water
  5. customdried under reduced pressure
  6. customAfter the completion of drying
  7. customwas obtained in the form of light yellow viscous material
  8. customThe characteristics absorption bands in the infrared spectrum of the thus obtained product

Sources & evidence

ORD record
ord-88d418ba6af24078a5d6d00bb4391f84
Source dataset
uspto-grants-1992_01
Patent number
US05084593

Reaction notes

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