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Pyridine → HCID 11795431, compound

HRID 431293
Notes
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Reaction equation

HRID 431293 reaction equation
ClC(Cl)(O[C:5](=[O:11])[O:6][C:7](Cl)(Cl)Cl)Cl.[CH3:13][CH:14]([OH:28])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26].N1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[CH3:35][C:36]#N.[C:38](=O)=[O:39]>C(Cl)Cl>[CH3:13][CH:14]([O:28][C:5]([O:6][C:7]1[C:33]([CH3:34])=[CH:32][C:31]([CH:38]=[O:39])=[CH:30][C:36]=1[CH3:35])=[O:11])[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[CH:17][C:16]=1[N+:25]([O-:27])=[O:26]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 1049Pyridine2×HCID 94429TriphosgeneHCID 27540461-(4,5-Dimethoxy-2-nitrophenyl)ethanolHCID 86587134Acetonitrile dry ice

Product 1

HCID 11795431HCID 11795431, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent
3×

Procedure

Triphosgene (0.224 g, 0.7 mmol) in CH2Cl2 (10 inL) at r.t. was added to a-methyl-2-nitro-4,5-dimethoxybenzyl alcohol (0.500 g, 2.2 mmol) and pyridine (0.534 inL, 6.6 mmol) in CH2Cl2 (20 mL) at −42 EC (CH3CN/CO2). After 2 hours, 4-hydroxy-3,5-diinethylbenzaldehyde (0.330 g, 2.2 mmol) and pyridine (0.534 mL, 6.6 inmol) in CH2Cl2 (10 mL) at r.t. was added and the mixture was allowed to slowly warm to r.t. overnight. The reaction mixture was quenched with saturated ammoniuin chloride (80 mL) and aqueous workup (CH2CI2, MgSO4) followed by concentration in vacuo afforded a brown solid which was recrystallized (EtOH) to yield 7k (431.9 mg, 49%) as a cream colored solid: 1H NMR (270 MHz, CDCl3) d 1.76 (d, J=6.4 Hz, 3H), 2.18 (s, 6H), 3.93 (s, 3H), 3.98 (s, 3H), 6.47 (q, J=6.4 Hz, 1H), 7.11 (s, 1H), 7.55 (s, 2H), 7.59 (s, 1H), 9.88 (s, 1H); 13C NMR (68 MHz, CDCl3) d 16.2, 22.0, 56.5, 56.6, 73.6, 107.5, 107.8, 130.4, 131.5, 132.0, 134.3, 140.1, 148.4, 151.2, 152.7, 153.8, 191.4.

Workup

  1. customThe reaction mixture was quenched with saturated ammoniuin chloride (80 mL) and aqueous workup (CH2CI2, MgSO4)
  2. concentrationfollowed by concentration in vacuo
  3. customafforded a brown solid which
  4. customwas recrystallized (EtOH)

Sources & evidence

ORD record
ord-d55325661b0b41f4811f152130d7e6ee
Source dataset
uspto-grants-2003_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06657052B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes