Hydrochloric Acid → HCID 10631479, compound

HRID 2229911Notes

Reaction equation

HRID 2229911 reaction equation
ClCC1C(C)=CC(C)=C(CCl)C=1C.[C-]#N.[Na+].[N-]=[N+]=[N-].[Na+].[C:21]([CH2:23][C:24]1[C:25]([CH3:36])=[C:26]([C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34])[CH2:27][N:28]=[N+]=[N-])#[N:22].C(CC1C(C)=CC(C)=C(CC#N)C=1C)#N.N(CC1C(C)=CC(C)=C(CN=[N+]=[N-])C=1C)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl.C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C1COCC1.O>[C:21]([CH2:23][C:24]1[C:25]([CH3:36])=[C:26]([C:31]([CH3:35])=[CH:32][C:33]=1[CH3:34])[CH2:27][NH2:28])#[N:22]

Participants

13

Reactant 9

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 33557Sodium AzideHCID 137095Benzene, 2,4-bis(chloromethyl)-1,3,5-trimethyl-HCID 10633221HCID 10633221, compoundHCID 10656266HCID 10656266, compoundHCID 10798029HCID 10798029, compound

Product 1

HCID 10631479HCID 10631479, compoundYield 25%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 1,3-bis(chloromethyl)-2,4,6-trimethylbenzene (10 g, 46 mmol) in DMSO (30 mL) was added sodium cyanide (2.25 g, 46 mmol). The mixture was stirred at rt overnight before sodium azide (4.5 g, 69 mmol) was added. The mixture was heated at 80° C. for 3 h before it was poured into water (300 mL). The resulting precipitate was filtered to give a 2:1:1.5 mixture of 3-cyanomethyl-2,4,6-trimethylbenzyl azide, 1,3-bis(cyanomethyl)-2,4,6-trimethylbenzene and 1,3-bis(azidomethyl)-2,4,6-trimethylbenzene. This mixture was not separated but was treated with triphenylphosphine (18 g, 69 mmol) in wet THF. The reaction was conducted and worked up as in Example 12 (procedure A) only that the HCl solution was basified with K2CO3 until no more gas evolution observed. The mixture was extracted with dichloromethane and concentrated to give only the desired 3-cyanomethyl-2,4,6-trimethylbenzylamine (2 g, 25% yield).

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was filtered
  3. customto give
  4. customThis mixture was not separated
  5. extractionThe mixture was extracted with dichloromethane
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5ad49338d883486aa5c9dfa2085354d4
Source dataset
uspto-grants-2002_07
Patent number
US06420567B1

Reaction notes

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