1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 14207562, compound

HRID 978360Notes

Reaction equation

HRID 978360 reaction equation
[C:1]([NH:6][C:7]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[C:12]([CH2:19][CH3:20])[C:8]=1[C:9]([OH:11])=[O:10])([O:3][CH2:4][CH3:5])=O.Cl.CN(C)CCCN=C=NCC>C1COCC1>[CH2:4]([O:3][C:1]1[O:10][C:9](=[O:11])[C:8]2[C:12]([CH2:19][CH3:20])=[CH:13][C:14]([N+:16]([O-:18])=[O:17])=[CH:15][C:7]=2[N:6]=1)[CH3:5]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13827108HCID 13827108, compound

Product 1

HCID 14207562HCID 14207562, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-carboethoxyamino-4-nitro-6-ethyl-benzoic acid and 1-(3-dimethylaminopropyl)-3-ethylcarbodimide hydrochloride in anhydrous THF (25 ml) was stirred at room temperature for 21/2 hrs. The solution was evaporated by dryness and the residue partitioned between ethyl acetate and water. The ethyl acetate layer was dried over magnesium sulphate and evaporated to a solid. The solid was recrystallized from methylene chloride: petroleum ether to give the title compound, 2-ethoxy-5-ethyl-7-nitro-4H-3,1-benzoxazin-4-one, m.p. 106°-107° C., Ir. 1770, 1660, 1600, 1595, 1535, 1515 cm.

Workup

  1. customThe solution was evaporated by dryness
  2. customthe residue partitioned between ethyl acetate and water
  3. dry with materialThe ethyl acetate layer was dried over magnesium sulphate
  4. customevaporated to a solid
  5. customThe solid was recrystallized from methylene chloride

Sources & evidence

ORD record
ord-9dda57ac09554224ba93f1c1b712cb96
Source dataset
uspto-grants-1987_05
Patent number
US04665070

Reaction notes

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