Hydrochloric Acid → HCID 54438405, compound

HRID 1156262Notes

Reaction equation

HRID 1156262 reaction equation
[CH:1]1([CH2:18][C:19]([C:21]2[S:25][C:24]([CH:26]=[CH:27][C:28]([O:30]CC)=[O:29])=[CH:23][CH:22]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.[OH-].[Na+].Cl>CCOCC>[CH:1]1([CH2:18][C:19]([C:21]2[S:25][C:24]([CH:26]=[CH:27][C:28]([OH:30])=[O:29])=[CH:23][CH:22]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 53937983HCID 53937983, compound

Product 1

HCID 54438405HCID 54438405, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 23.0 g (0.05 mole) of the above ester and 250 ml of ethanol are heated to reflux, 100 ml of 1 N aqueous sodium hydroxide is added and the mixture refluxed for 3 hours, then cooled to room temperature. The mixture is acidified to pH 1 with 1 N hydrochloric acid, ether is added and the layers separated. The ether layer is washed with water and evaporated to dryness to give 3-[5-(cycloheptadecylacetyl)-2-thienyl]-2-propenoic acid. This acid is added to 6.9 g (0.06 mole) of α,α-dichloromethyl methyl ether in 100 ml of dichloromethane. The mixture is refluxed overnight then evaporated to dryness to give the corresponding acid chloride which is added to 200 ml of tetrahydrofuran. To the above mixture is added 100 ml of strong ammonium hydroxide solution. The mixture is stirred overnight, is diluted with 500 ml of water and filtered. The precipitate is washed with water and dried to give 3-[5 -(cycloheptadecylacetyl)-2-thienyl]-2-propenamide.

Workup

  1. temperatureare heated
  2. temperatureto reflux
  3. temperaturethe mixture refluxed for 3 hours
  4. additionis added
  5. customthe layers separated
  6. washThe ether layer is washed with water
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-94ff772a32f74909830ab1813f5637ab
Source dataset
uspto-grants-1982_06
Patent number
US04335098

Reaction notes

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