Water → HCID 67397986, compound

HRID 1990704Notes

Reaction equation

HRID 1990704 reaction equation
C(N(CC)CC)C.[CH2:8]([OH:13])[CH2:9][CH2:10][C:11]#[CH:12].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21](Cl)=[N:22][OH:23])=[CH:17][CH:16]=1.O>ClCCl>[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:12]=[C:11]([CH2:10][CH2:9][CH2:8][OH:13])[O:23][N:22]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 793464-Pentyn-1-olHCID 27555434-chloro-N-hydroxybenzene-1-carbonimidoyl chloride

Product 1

HCID 67397986HCID 67397986, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.6 ml (11.5 mmol) of triethylamine are added dropwise to a solution, cooled with an ice bath, of 1.18 ml (12.6 mmol) of pent-4-yn-1-ol and of 2.0 g (10.5 mmol) of 4-chloro-N-hydroxybenzenecarboximidoyl chloride (J. Med. Chem., 1998, 41, 4556-4566) in 30 ml of dichloromethane. Reaction is allowed to take place at ambient temperature overnight. 50 ml of dichloromethane and 70 ml of water are added. The organic phase is separated and the aqueous phase is extracted with 2 times 50 ml of dichloromethane. The organic phases are subsequently washed with 2 times 70 ml of water and then with 70 ml of a saturated aqueous sodium chloride solution, dried over sodium sulphate and evaporated. The residue is purified by chromatography on silica gel, elution being carried out with a mixture of cyclohexane and of ethyl acetate, to produce 1.3 g (5.47 mmol) of product in the form of a white solid.

Workup

  1. customReaction
  2. customat ambient temperature
  3. customovernight
  4. customThe organic phase is separated
  5. extractionthe aqueous phase is extracted with 2 times 50 ml of dichloromethane
  6. washThe organic phases are subsequently washed with 2 times 70 ml of water
  7. dry with materialwith 70 ml of a saturated aqueous sodium chloride solution, dried over sodium sulphate
  8. customevaporated
  9. customThe residue is purified by chromatography on silica gel, elution
  10. additionbeing carried out with a mixture of cyclohexane and of ethyl acetate

Sources & evidence

ORD record
ord-27238af05a3043c6ae92e0ae5e91bc3b
Source dataset
uspto-grants-2010_01
Patent number
US07645757B2

Reaction notes

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