Hydrochloric Acid → HCID 20183530, compound

HRID 255509Notes

Reaction equation

HRID 255509 reaction equation
[OH:1][C:2]1[C:10]([CH2:11][CH2:12][CH3:13])=[C:9]2[C:5]([CH:6]=[C:7]([C:14]([O:16]CC)=[O:15])[NH:8]2)=[CH:4][CH:3]=1.[C:19]([C:25](OC)=[O:26])#[C:20][C:21]([O:23]C)=[O:22].[OH-].[Na+].Cl>C(O)C.O>[O:26]=[C:25]1[C:3]2[CH:4]=[C:5]3[C:9](=[C:10]([CH2:11][CH2:12][CH3:13])[C:2]=2[O:1][C:20]([C:21]([OH:23])=[O:22])=[CH:19]1)[NH:8][C:7]([C:14]([OH:16])=[O:15])=[CH:6]3

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12980Dimethyl acetylenedicarboxylateHCID 14798Sodium HydroxideHCID 20183534HCID 20183534, compound

Product 1

HCID 20183530HCID 20183530, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The product of step (c) (0.6 g, 0.0024 M), dimethyl acetylene dicarboxylate (0.33 ml, 0.0027 M) and "Triton B" (2 drops) were heated under reflux for 6 hours in dry ethanol (10 ml). The reaction mixture was cooled, NaOH (0.6 g, 14.6 mmol) in water (6 ml) was added and refluxing continued for 1 hour. The whole was cooled, poured into dil. HCl, extracted into ethyl acetate and washed with brine before drying over MgSO4 and evaporating to dryness to yield the sub-title compound as a pale yellow solid, 0.7 g, (86%).

Workup

  1. temperatureThe reaction mixture was cooled
  2. temperaturerefluxing
  3. temperatureThe whole was cooled
  4. extractionextracted into ethyl acetate
  5. washwashed with brine
  6. dry with materialbefore drying over MgSO4
  7. customevaporating to dryness

Sources & evidence

ORD record
ord-e81a767ea03246699b9899c48f4b1a17
Source dataset
uspto-grants-1987_10
Patent number
US04698345

Reaction notes

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