Dodecanoyl chloride → HCID 20431900, compound

HRID 2412637Notes

Reaction equation

HRID 2412637 reaction equation
[C:1](Cl)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[Br-:15].[NH2:16][C:17]1[CH:42]=[C:41]([C:43]([O:45][CH3:46])=[O:44])[CH:40]=[CH:39][C:18]=1[CH2:19][P+:20]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[Br-:15].[CH3:46][O:45][C:43]([C:41]1[CH:40]=[CH:39][C:18]([CH2:19][P+:20]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:17]([NH:16][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH:42]=1)=[O:44]

Participants

4

Reactant 2

HCID 8166Dodecanoyl chlorideHCID 20431922HCID 20431922, compound

Product 1

HCID 20431900HCID 20431900, compoundYield 73.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

n-Dodecanoyl chloride (9.9 g) was added dropwise to a stirred suspension of (2-amino-4-methoxycarbonylbenzyl)triphenylphosphonium bromide (22.9 g) in dry dimethylformamide (225 ml) and stirring continued for 3 hours. The resulting solution was evaporated in vacuo to give an orangebrown oil which on treatment with water gave a solid. The solid was collected, washed with water, dried, washed with diethyl ether and collected to give [4-methoxycarbonyl-2-(n-dodecanamido)benzyl]triphenylphosphonium bromide (22.9 g) in the form of a pale yellow solid, m.p. 142°-145° C.

Workup

  1. customThe resulting solution was evaporated in vacuo
  2. customto give an orangebrown oil which on treatment with water
  3. customgave a solid
  4. customThe solid was collected
  5. washwashed with water
  6. customdried
  7. washwashed with diethyl ether
  8. customcollected

Sources & evidence

ORD record
ord-ddd2a6fa8c2445228797dd6824b7b6d0
Source dataset
uspto-grants-1985_01
Patent number
US04493843

Reaction notes

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