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Diazald → HCID 54204114, compound

HRID 372893
Notes
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Reaction equation

HRID 372893 reaction equation
[N+:1](=[CH2:3])=[N-:2].CC1C=CC(S(N(N=O)C)(=O)=O)=CC=1.[OH-].[K+].Cl[C:21]([CH:23]([CH2:35][CH2:36][CH2:37][CH:38]([O:44][C:45](=[O:47])[CH3:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:22]>CCOCC.CCOCCOCCO.O>[N+:1](=[CH:3][C:21]([CH:23]([CH2:35][CH2:36][CH2:37][CH:38]([O:44][C:45](=[O:47])[CH3:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=[O:22])=[N-:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 6628DiazaldHCID 9550Diazomethane2×HCID 14797Potassium HydroxideHCID 20322197Ethyl 12-(acetyloxy)-8-(chlorocarbonyl)heptadecanoate

Product 1

HCID 54204114HCID 54204114, compound

Reagents, catalysts & solvents 2

HCID 3283
Diethyl Ether
Solvent
2×
HCID 131711019HCID 131711019, compoundSolvent

Procedure

Diazomethane (6 g., 0.143 mole) is generated via dropwise addition of a solution of Diazald® (43 g.) in ether (400 ml.) over 45 minutes to a warm (65%), stirred solution of potassium hydroxide (12 g., 0.214 mole) in carbitol-water (7:2, 90 ml.). The resulting yellow, ethereal diazomethane distillate is cooled to 0° and treated with a solution of ethyl 8-chlorocarbonyl-12-acetoxyheptadecanoate (8.1 g., 0.02 mole) (Example 7, Step D), in ether (40 ml.) added over a period of 15 minutes.

Workup

  1. temperaturea warm (65%)
  2. additionadded over a period of 15 minutes

Sources & evidence

ORD record
ord-2d375fd93223485492452c20ac0499ef
Source dataset
uspto-grants-1978_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04092356

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes