Aniline → HCID 69666449, compound

HRID 1791053Notes

Reaction equation

HRID 1791053 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.[Cl:26][CH:27]=[C:28]1[CH:34]=[CH:33][C:32]2[CH:35]=[C:36]([C:39](O)=[O:40])[CH:37]=[CH:38][C:31]=2[O:30][CH2:29]1>CO>[Cl:26][CH:27]=[C:28]1[CH:34]=[CH:33][C:32]2[CH:35]=[C:36]([C:39]([NH:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:40])[CH:37]=[CH:38][C:31]=2[O:30][CH2:29]1

Participants

5

Reactant 3

HCID 6115AnilineHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 69666585HCID 69666585, compound

Product 1

HCID 69666449HCID 69666449, compoundYield 15.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

127 mg (0.46 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride and then 39 mg (0.42 mmol) of aniline are added to 100 mg (0.42 mmol) of 3-(chloromethylene)-2,3-dihydro-1-benzoxepin-7-carboxylic acid, prepared according to example 63, in solution in 4 ml of methanol, and the medium is stirred at ambient temperature for 3 hours. The methanol is evaporated and the crude reaction product is purified by chromatography on silica gel (ethyl acetate/heptane 40/60) to give 20 mg (15%) of 3-(chloromethylene)-N-phenyl-2,3-dihydro-1-benzoxepin-7-carboxamide in the form of a pink solid comprising two Z/E isomers as a mixture in an 85/15 ratio; mass (APCI) M+1=312.

Workup

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

Sources & evidence

ORD record
ord-a0cccb0dc3ef4d53b68c107a8f87a28f
Source dataset
uspto-grants-2006_07
Patent number
US07071340B2

Reaction notes

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