2-Methylbenzylamine → HCID 13912532, compound

HRID 1788821Notes

Reaction equation

HRID 1788821 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5](Cl)=[O:6].CC1C=C(C=C(C)C=1[N+]([O-])=O)C(O)=O.[CH3:29][C:30]1[CH:37]=[CH:36][CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33].C(N(CC)CC)C>O1CCCC1>[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:14])[C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([NH:33][CH2:32][C:31]1[CH:34]=[CH:35][CH:36]=[CH:37][C:30]=1[CH3:29])=[O:6]

Participants

6

Reactant 4

HCID 69932-MethylbenzylamineHCID 8471TriethylamineHCID 2494133,5-Dimethyl-4-nitrobenzoic acidHCID 123321313,5-Dimethyl-4-nitrobenzoyl chloride

Product 1

HCID 13912532HCID 13912532, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3,5-dimethyl-4-nitrobenzoyl chloride in tetrahyrofuran, generated from 7.0 g of 3,5-dimethyl-4-nitrobenzoic acid by standard procedures, was added to 4.3 g of 2-methylbenzyl amine and 5.0 ml of triethylamine in tetrahydrofuran. The reaction was stirred at ambient temperature overnight, chilled, and filtered. The filtrate was evaporated in vacuo and the residue therefrom was dissolved in chloroform, washed sequentially with 1N hydrochloric acid, 1N sodium hydroxide, water, and a saturated sodium chloride solution, dried over sodium sulfate, filtered, and evaporated in vacuo. Crystallization from methanol/water provided 4.7 g of the desired title product, m.p. 202°-203° C.

Workup

  1. temperaturechilled
  2. filtrationfiltered
  3. customThe filtrate was evaporated in vacuo
  4. dissolutionthe residue therefrom was dissolved in chloroform
  5. washwashed sequentially with 1N hydrochloric acid, 1N sodium hydroxide, water
  6. dry with materiala saturated sodium chloride solution, dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customCrystallization from methanol/water

Sources & evidence

ORD record
ord-5f1172c237c240db90b4e91212b88ef5
Source dataset
uspto-grants-1987_08
Patent number
US04684748

Reaction notes

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