Water → HCID 13752194, compound

HRID 365071Notes

Reaction equation

HRID 365071 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])=O.[NH2:13][C:14]([CH3:21])([CH:18]([CH3:20])[CH3:19])[C:15]([NH2:17])=[O:16].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[C:15]([C:14]([N:13]=[CH:1][C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([O:7][CH3:8])=[O:6])([CH3:21])[CH:18]([CH3:20])[CH3:19])(=[O:16])[NH2:17]

Participants

6

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 243003Methyl 2-formylbenzoateHCID 97937732-Amino-2,3-dimethylbutanamide

Product 1

HCID 13752194HCID 13752194, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture containing 5.0 g methyl 2-formylbenzoate [C. Brown and M. V. Sargent, J. Chem. Soc. (C), 1818 (1969)] and 4.0 g 2-amino-2,3-dimethylbutyramide and 50 mg p-toluenesulfonic acid in 100 mL toluene is heated under reflux under a Dean-Stark water separator for three hours. The mixture is filtered and concentrated in vacuo. The residue crystallizes on standing and is recrystallized from etherhexane to give analytically pure methyl o-[N-(1-carbamoyl-1,2-dimethylpropyl)formimidoyl]benzoate, mp 79°-80.5° C.

Workup

  1. temperatureis heated
  2. filtrationThe mixture is filtered
  3. concentrationconcentrated in vacuo
  4. customThe residue crystallizes on standing
  5. customis recrystallized from etherhexane

Sources & evidence

ORD record
ord-166ff1308d184c4c9c50392ff7b21f23
Source dataset
uspto-grants-1986_08
Patent number
US04608079

Reaction notes

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