1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 14207564, compound

HRID 1252734Notes

Reaction equation

HRID 1252734 reaction equation
[CH:1]([O:4][C:5]([NH:7][C:8]1[CH:16]=[C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:14]=[C:13]([CH3:25])[C:9]=1[C:10]([OH:12])=[O:11])=O)([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH:1]([O:4][C:5]1[O:11][C:10](=[O:12])[C:9]2[C:13]([CH3:25])=[CH:14][C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:16][C:8]=2[N:7]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 14207580HCID 14207580, compound

Product 1

HCID 14207564HCID 14207564, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 2-(isopropoxy)carbonylamino-4-benzyloxy-6-methyl-benzoic acid (97 mg, 0.000282 mol) and 1-(3-dimethylaminopropyl)-3-ethyl-carbodiimide hydrochloride (EDCI) (200 mg) in methylene chloride (20 ml) was stirred at room temperature for 2 days. The solution was diluted with methylene chloride and extracted with water. The methylene chloride was further washed with brine solution, dried over sodium sulphate and evaporated to give a yellow solid. This material was further purified by column chromatography (5% ethyl acetate: pet. ether 30-60) to give 2-isopropoxy-5-methyl-7-benzyloxy-4H-3,1-benzoxazin-4-one (55 mg), m.p. 137°-138° C., IR (CHCl3): 1755, 1640, 1605, 1569, 1460 cm-1. H--NMR (CDCl3): 1.4 (d, 6H, CH3CHCH3), 2.7 (s, 3H, CH3), 5.15 (s, 2H, OCH2Ph), 5.30 (p, 1H, CH), 6.8 (s, 1H, ArH), 7.40 (s, 5H, Ph).

Workup

  1. extractionextracted with water
  2. washThe methylene chloride was further washed with brine solution
  3. dry with materialdried over sodium sulphate
  4. customevaporated
  5. customto give a yellow solid
  6. customThis material was further purified by column chromatography (5% ethyl acetate: pet. ether 30-60)

Sources & evidence

ORD record
ord-613f180c93f8413d8ed6598da1a540da
Source dataset
uspto-grants-1988_05
Patent number
US04745116

Reaction notes

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