Ammonia → HCID 54246851, compound

HRID 1583909Notes

Reaction equation

HRID 1583909 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:52])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:51])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:50])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:49])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:48])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:47])[CH2:31][CH2:32][CH:33]=[C:34]([CH3:46])[CH2:35][CH2:36][CH:37]=[C:38]([CH3:45])[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])[CH2:3][C:4](O)=[O:5].[NH3:53].C1C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl>[CH3:1][CH:2]([CH2:7][CH2:8][CH:9]=[C:10]([CH3:52])[CH2:11][CH2:12][CH:13]=[C:14]([CH3:51])[CH2:15][CH2:16][CH:17]=[C:18]([CH3:50])[CH2:19][CH2:20][CH:21]=[C:22]([CH3:49])[CH2:23][CH2:24][CH:25]=[C:26]([CH3:48])[CH2:27][CH2:28][CH:29]=[C:30]([CH3:47])[CH2:31][CH2:32][CH:33]=[C:34]([CH3:46])[CH2:35][CH2:36][CH:37]=[C:38]([CH3:45])[CH2:39][CH2:40][CH:41]=[C:42]([CH3:44])[CH3:43])[CH2:3][C:4]([NH2:53])=[O:5]

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 21583983Benzene ethyl acetateHCID 53967098HCID 53967098, compound

Product 1

HCID 54246851HCID 54246851, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

20 g of 3,7,11,15,19,23,27,31,35,39-decamethyl-6,10,14,18,22,26,30,34,38-tetracontanonaenic acid are dissolved in 100 ml of methylene chloride. To this solution, 6.9 g of N,N-dicyclohexylcarbodiimide are added with cooling at 0° C., and stirred for 1.0 hour. Ammonia gas is blown little by little into this solution during an hour. Stirring for 3.0 hours is performed at room temperature after the end of addition of ammonia. Mother liquor is condensed after filtering off N,N-dicyclohexylurea formed. The residue is subjected to silica gel column chromatography using benzene/ethyl acetate mixture for eluting solvent. The desired product was obtained as an oily substance light yellow in color (yield: 12.3 g). This oily substance was dissolved in 50 ml of acetone and left overnight in a refrigerator. The white crystals deposited were filtered off, dried and thus yielded 8.5 g of desired final product, acid amide derivative.

Workup

  1. customduring an hour
  2. stirringStirring for 3.0 hours
  3. customis performed at room temperature
  4. customcondensed
  5. filtrationafter filtering off N,N-dicyclohexylurea
  6. customformed
  7. washfor eluting solvent

Sources & evidence

ORD record
ord-8c461ce6b883472081ca17ec3d5b46da
Source dataset
uspto-grants-1985_11
Patent number
US04555365

Reaction notes

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