Acetyl chloride → HCID 22447914, compound

HRID 2188369Notes

Reaction equation

HRID 2188369 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9](N(C)C)[N:10]([CH3:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1.C([Cl:19])(=O)C>CCOCC.CO.C[C@H]1O[C@H]2[C@H](O)[C@@H](O)[C@H](OC3C4C(=CC5OCOC=5C=4)[C@@H](C4C=C(OC)C(O)=C(OC)C=4)[C@@H]4[C@@H]3COC4=O)O[C@@H]2CO1.C1COP(NCCCl)(=O)N(CCCl)C1.[NH2-].[NH2-].Cl[Pt+2]Cl>[Cl-:19].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[CH:7][CH:8]=1)[CH:9]=[N+:10]([CH3:12])[CH3:11]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 22447879HCID 22447879, compound

Product 1

HCID 22447914HCID 22447914, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 131723329HCID 131723329, compoundCatalystHCID 3283Diethyl EtherSolvent

Procedure

30 g (144 mmole) of C-(3-methoxyphenyl)-N,N,N′,N′-tetramethylmethanediamine from stage 1 were dissolved in 200 ml of ether and cooled in an ice bath (methanol/ice 1:1) to −10° C. 10.3 ml (144 mmole) of acetyl chloride were added dropwise under nitrogen. A white salt precipitated out, and the temperature rose slightly. After 15 hours at RT the solution was decanted off, and the solids were washed three times, each time with 100 ml of ether, filtered through a protective gas frit under nitrogen, and dried to constant weight in an oil pump vacuum. 19.8 g of (3-methoxybenzylidene)dimethyl ammonium chloride (68.8% of theory) were obtained in this way.

Workup

  1. customA white salt precipitated out
  2. customAfter 15 hours at RT the solution was decanted off
  3. washthe solids were washed three times
  4. filtrationeach time with 100 ml of ether, filtered through a protective gas frit under nitrogen
  5. customdried to constant weight in an oil pump vacuum

Sources & evidence

ORD record
ord-f4b9307952564fdb80358836d3fdbb96
Source dataset
uspto-grants-2002_06
Patent number
US06410790B1

Reaction notes

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