Hydrochloric Acid → HCID 70299391, compound

HRID 863555Notes

Reaction equation

HRID 863555 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][CH:14]=[C:15]2[C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[S:22][C:21]3[C:16]2=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:32]CCl>C(O)C>[ClH:32].[CH:17]1[C:16]2[C:15](=[CH:14][CH2:13][CH2:12][N:8]3[CH2:9][CH2:10][CH2:11][CH:6]([C:4]([OH:5])=[O:3])[CH2:7]3)[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[S:22][C:21]=2[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 50852542HCID 50852542, compound

Product 1

HCID 70299391HCID 70299391, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The above ester (0.74 g, 1.8 mmol) was dissolved in ethanol (25 ml) and 40% sodium hydroxide (6 ml) was added. The mixture was heated at reflux for 1 h. 10% Hydrochloric acid (25 ml) was added followed by dichloromethane (150 ml). The phases were separated and the organic phase was washed with water, dried (NaSO4) and the solvent was evaporated in vacuo to give 0.6 g of the title compound as a solid. M.p. 150°-160° C. A sample was dissolved in acetone and precipitated with diethyl ether. The solid formed was isolated by filtration and dried in vacuo.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 1 h
  3. customThe phases were separated
  4. washthe organic phase was washed with water
  5. dry with materialdried (NaSO4)
  6. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-025e88196f9b4853a90af592b2950efb
Source dataset
uspto-grants-1998_02
Patent number
US05721254

Reaction notes

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