Ethyl isocyanate → HCID 14390920, compound

HRID 2292281Notes

Reaction equation

HRID 2292281 reaction equation
Cl.Cl.[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]([C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:11][CH2:12][CH2:13][N:14]2[CH2:20][CH2:19][NH:18][NH:17][CH2:16][CH2:15]2)=[CH:6][CH:5]=1.C(N(CC)C(C)C)(C)C.[CH2:37]([N:39]=[C:40]=[O:41])[CH3:38]>ClCCl>[F:27][C:24]1[CH:23]=[CH:22][C:21]([CH:10]([C:7]2[CH:8]=[CH:9][C:4]([F:3])=[CH:5][CH:6]=2)[CH2:11][CH2:12][CH2:13][N:14]2[CH2:15][CH2:16][N:17]([C:40]([NH:39][CH2:37][CH3:38])=[O:41])[NH:18][CH2:19][CH2:20]2)=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8022Ethyl isocyanateHCID 81531DiisopropylethylamineHCID 21277222HCID 21277222, compound

Product 1

HCID 14390920HCID 14390920, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-[4,4-bis(4-fluorophenyl)butyl]hexahydro-1H-1,2,5-triazepine dihydrochloride (3.25 g, prepared as in example 13), N,N-diisopropylethylamine (3.38 ml) in dry dichloromethane (10 ml) at 5° under nitrogen was added ethyl isocyanate (0.62 ml) in dichloromethane (10 ml) and the solution was stirred at room temperature overnight. After extraction of the mixture with water, the dichloromethane solution was dried (Na2SO4) and evaporated to an oil. The crude product was chromatographed on a column of silica gel prepacked in dichloromethane. Successive elution with ethyl acetate-dichloromethane (4:1) and ethanol-ethyl acetate-dichloromethane (1:4:5) allowed a separation of a major component from impurities. The hydrobromide salt of the titled compound was formed from the material in 2-propanol and was recrystallized from 2-propanol-ethyl acetate; wt. 2.18 g (49%), mp=130°-134° dec.

Workup

  1. extractionAfter extraction of the mixture with water
  2. dry with materialthe dichloromethane solution was dried (Na2SO4)
  3. customevaporated to an oil
  4. customThe crude product was chromatographed on a column of silica gel
  5. washSuccessive elution with ethyl acetate-dichloromethane (4:1) and ethanol-ethyl acetate-dichloromethane (1:4:5)
  6. customa separation of a major component from impurities

Sources & evidence

ORD record
ord-97f65b35bedc4420b569d424ee78b8ca
Source dataset
uspto-grants-1989_01
Patent number
US04801706

Reaction notes

Loading…