N,N-Dimethylaniline → HCID 57258309, compound

HRID 1863153Notes

Reaction equation

HRID 1863153 reaction equation
[C:1]([CH2:3][NH:4][C:5](=[O:9])[C:6](Cl)=[O:7])#[N:2].[CH:10]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=[C:12]([OH:19])[CH:11]=1.CN(C)C1C=CC=CC=1>C(Cl)Cl>[C:1]([CH2:3][NH:4][C:5](=[O:9])[C:6]([O:19][C:12]1[CH:11]=[CH:10][C:15]([N+:16]([O-:18])=[O:17])=[CH:14][CH:13]=1)=[O:7])#[N:2]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 9804-NitrophenolHCID 20392174HCID 20392174, compound

Product 1

HCID 57258309HCID 57258309, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

50 mM of [(cyanomethyl)amino]oxoacetyl chloride dissolved in methylene chloride is added dropwise at 0° to a solution of 40 mM of p-nitrophenol and 40 mM of dimethylaniline in methylene chloride. After stirring for one hour, the reaction mixture is extracted once with dilute hydrochloric acid and twice with water. The dried methylene chloride phase is concentrated under vacuum and yields 4.2 g. of [(cyanomethyl)amino]-oxoacetic acid, 4-nitrophenyl ester as a brown oil which crystallizes upon trituration with ether. Recrystallization from toluene gives white crystals, m.p. 123-124°.

Workup

  1. extractionthe reaction mixture is extracted once with dilute hydrochloric acid and twice with water
  2. concentrationThe dried methylene chloride phase is concentrated under vacuum
  3. customyields 4.2 g
  4. customof [(cyanomethyl)amino]-oxoacetic acid, 4-nitrophenyl ester as a brown oil which crystallizes upon trituration with ether
  5. customRecrystallization from toluene
  6. customgives white crystals, m.p. 123-124°

Sources & evidence

ORD record
ord-d33b3e4933d643199c7d6de4b221e3bb
Source dataset
uspto-grants-1979_09
Patent number
US04168266

Reaction notes

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