Triethylamine → HCID 86744763, compound

HRID 2050561Notes

Reaction equation

HRID 2050561 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:16]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=[C:13]3[C:10]=2[CH2:11][CH:12]3[C:25](O)=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N([CH2:33][CH3:34])CC)C.Cl[C:36]([O:38][CH2:39][CH3:40])=O.[CH2:41]([NH2:48])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][NH2:47]>ClCCl>[C:1]1([CH2:7][O:8][C:9]2[C:16]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[CH:15][CH:14]=[C:13]3[C:10]=2[CH2:11][CH:12]3[C:25]([NH:47][CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][NH:48][C:25]([CH:12]2[CH2:11][C:10]3[C:13]2=[CH:14][CH:15]=[C:16]([O:17][CH2:18][C:34]2[CH:33]=[CH:24][CH:19]=[CH:20][CH:21]=2)[C:36]=3[O:38][CH2:39][C:40]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)=[O:26])=[O:26])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 16402HexamethylenediamineHCID 12789358HCID 12789358, compound

Product 1

HCID 86744763HCID 86744763, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,3-Bis-(phenylmethoxy)-bicyclo-[4.2.0]-octa-1,3,5-triene-7-carboxylic acid (0.72 g) was dissolved in dry dichloromethane (40 ml) and cooled to -5° and triethylamine (0.31 ml) added. To this was added a solution of ethyl chloroformate (0.19 ml) in dry dichloromethane (2 ml) dropwise over 10 minutes. The solution was stirred at -5° for 1 hour and hexane-1,6-diamine (0.11 g) added and the mixture warmed to room temperature for 4 hours. The reaction mixture was washed with water, 2N hydrochloric acid, 2N sodium hydroxide solution and brine dried (Na2SO4) and evaporated. The residue was recrystallised from ethanol affording the purified bis amide (0.43 g) mp 155°-9°.

Workup

  1. temperaturecooled to -5°
  2. washThe reaction mixture was washed with water, 2N hydrochloric acid, 2N sodium hydroxide solution and brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was recrystallised from ethanol affording the purified bis amide (0.43 g) mp 155°-9°

Sources & evidence

ORD record
ord-99b22df5caf945f88832a9e3040944b1
Source dataset
uspto-grants-1991_05
Patent number
US05013760

Reaction notes

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