Hydrochloric Acid → HCID 69114589, compound

HRID 916535Notes

Reaction equation

HRID 916535 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:13]=[C:14]([Cl:16])[CH:15]=1)[O:5][CH:6]([CH2:10][O:11][CH3:12])[C:7]([OH:9])=O.C(Cl)(=O)C(Cl)=O.ClC1C=C(C(COC)C(Cl)=O)C=C(Cl)C=1.Cl.[NH2:39][C:40]([CH3:45])([CH3:44])[C:41]#[C:42][CH3:43].Cl>ClCCl.O.C(OCC)(=O)C.CCCCCC.C(N(CC)CC)C>[Cl:16][C:14]1[CH:13]=[C:4]([CH:3]=[C:2]([Cl:1])[CH:15]=1)[O:5][CH:6]([CH2:10][O:11][CH3:12])[C:7]([NH:39][C:40]([CH3:45])([CH3:44])[C:41]#[C:42][CH3:43])=[O:9]

Participants

11

Reactant 5

HCID 313Hydrochloric AcidHCID 65578Oxalyl chlorideHCID 219231292-Methylpent-3-yn-2-amine hydrochlorideHCID 69114724701915-91-5HCID 876999982-(3,5-Dichlorophenyl)-3-methoxypropionic acid chloride

Product 1

HCID 69114589HCID 69114589, compound

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The product from Stage 3 (0.44 g) was dissolved in dry dichloromethane (10 ml) with stirring and oxalyl chloride (0.212 g) was added. When no further gas was evolved the mixture was evaporated under reduced pressure to give a pale yellow oil which contained 2-(3,5-dichlorophenyl)-3-methoxypropionic acid chloride. The acid chloride was dissolved in dry dichloromethane (5 ml) and 4-amino-4-methylpent-2-yne hydrochloride (prepared as described below; 0.222 g) was added. The suspension was stirred at ambient temperature whilst triethylamine (0.48 ml) was added dropwise. The mixture was stirred for 3 hours, diluted with water, acidified with dilute aqueous hydrochloric acid (2M) then extracted with further dichloromethane. The organic extract was separated, washed with brine then dried over magnesium sulphate and evaporated under reduced pressure to give a gum. The gum was fractionated by chromatography (silica; hexane:ethyl acetate, 3:1 by volume) to give the required product as a colourless solid, 0.28 g, mp 107-110° C.

Workup

  1. customwas evaporated under reduced pressure
  2. customto give a pale yellow oil which
  3. additionwas added dropwise
  4. stirringThe mixture was stirred for 3 hours
  5. extractionthen extracted with further dichloromethane
  6. extractionThe organic extract
  7. customwas separated
  8. washwashed with brine
  9. dry with materialthen dried over magnesium sulphate
  10. customevaporated under reduced pressure
  11. customto give a gum

Sources & evidence

ORD record
ord-4c3700d956db4204a80b5b9877672a07
Source dataset
uspto-grants-2007_09
Patent number
US07271130B2

Reaction notes

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