Triethylamine → HCID 12109280, compound

HRID 2268912Notes

Reaction equation

HRID 2268912 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH:6]=O.[Br-].[CH3:10][O:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[CH:17]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)O[C:15]2=[O:40].C(N(CC)CC)C.O.[NH2:49][NH2:50]>C(Cl)Cl.O.C(O)C>[CH3:1][O:2][C:3](=[O:8])[CH2:4][CH2:5][CH2:6][C:17]1[C:18]2[C:14](=[CH:13][C:12]([O:11][CH3:10])=[CH:20][CH:19]=2)[C:15](=[O:40])[NH:50][N:49]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 83779Methyl 4-oxobutyrateHCID 11562468(5-Methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide

Product 1

HCID 12109280HCID 12109280, compoundYield 75.7%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-formyl-propionic acid methyl ester (13.4 g, 0.1155 moles) and (5-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide (55.6 g, 0.11 moles), prepared as described in example 36, in CH2Cl2 (440 ml) in water bath was dropwise added with triethylamine (16.1 ml, 0.1155 mole). At the end of the addition the mixture was stirred at room temperature overnight, then washed with water, anhydrified and dried to give a residue which was taken up in ethanol (180 ml). The solution was cooled and added with hydrazine monohydrate (11 g, 0.22 mole). A precipitate formed and was filtered. After 6 days the mother liquors gave a precipitate which joined to the previous one yielded 23 g of the title compound (yield: 75.5%). m.p.: 175-177° C.

Workup

  1. additionAt the end of the addition the mixture
  2. washwashed with water
  3. customdried
  4. customto give a residue which
  5. temperatureThe solution was cooled
  6. customA precipitate formed
  7. filtrationwas filtered
  8. customAfter 6 days the mother liquors gave a precipitate which

Sources & evidence

ORD record
ord-da937f28d8374ded8ed9e80aeb2c8318
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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