Phosphorus oxychloride → N,N-dioctadecylaminobenzaldehyde

HRID 414443Notes

Reaction equation

HRID 414443 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([N:24]([CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].[C:49]([O-])(=[O:51])C.[Na+]>CN(C)C=O>[CH2:31]([N:24]([C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=1[CH:49]=[O:51])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 4106142N,N-Dioctadecylaniline

Product 1

HCID 53874326N,N-dioctadecylaminobenzaldehydeYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

Phosphorus oxychloride (15.3 g, 0.1 mole) was added dropwise with stirring, at 5° C., under nitrogen, to N,N-dimethylformamide (DMF, 50 mL). The resulting orange solution was stirred for 2 hours, then 42 g (0.08 mole) of N,N-dioctadecylaniline was added all at once. The reaction mixture was heated in a water bath to 90° C., and stirring was continued for 4 hours. The hot solution was poured over 200 g of crushed ice and naturalized to pH 6 by a slow addition of solid sodium acetate with vigorous stirring. The greenish-tint crystalline precipitate was filtered by suction, washed with water on the filter and air dried. The light green product was recrystallized from isopropanol to yield 46.5 g (93%) of pale-green crystals mp 65°-66° C.

Workup

  1. stirringstirring
  2. waitwas continued for 4 hours
  3. filtrationThe greenish-tint crystalline precipitate was filtered by suction
  4. washwashed with water on the
  5. filtrationfilter
  6. customair dried
  7. customThe light green product was recrystallized from isopropanol

Sources & evidence

ORD record
ord-5cf81c4ea3a0411787581e0d066285c1
Source dataset
uspto-grants-1988_12
Patent number
US04792208

Reaction notes

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