Aniline → 3-methylene-N-phenyl-2,3-dihydro-1-benzoxepin-7-carboxamide

HRID 1791047Notes

Reaction equation

HRID 1791047 reaction equation
[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:26]=[C:27]1[CH:33]=[CH:32][C:31]2[CH:34]=[C:35]([C:38](O)=[O:39])[CH:36]=[CH:37][C:30]=2[O:29][CH2:28]1>CO>[CH2:26]=[C:27]1[CH:33]=[CH:32][C:31]2[CH:34]=[C:35]([C:38]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:39])[CH:36]=[CH:37][C:30]=2[O:29][CH2:28]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 220422573-Methylene-2,3-dihydro-1-benzoxepin-7-carboxylic acid

Product 1

HCID 220422703-methylene-N-phenyl-2,3-dihydro-1-benzoxepin-7-carboxamideYield 49%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.12 g (4.07 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride and then 0.379 g (4.07 mmol) of aniline are successively added to 0.75 g (3.7 mmol) of 3-methylene-2,3-dihydro-1-benzoxepin-7-carboxylic acid, prepared according to example 40, in solution in 25 ml of methanol. The medium is stirred at ambient temperature for 24 h. After evaporating the methanol, the crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 40/60) to give 185 mg (49%) of 3-methylene-N-phenyl-2,3-dihydro-1-benzoxepin-7-carboxamide in the form of a pink solid; M.p.=139° C.

Workup

  1. customprepared
  2. customAfter evaporating the methanol
  3. customthe crude reaction product
  4. customis purified by chromatography on silica gel (ethyl acetate/heptane 40/60)

Sources & evidence

ORD record
ord-d7c1f62e8e2547cea838bf05bb3c09f8
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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