Hydrochloric Acid → HCID 178423802, compound

HRID 1627938Notes

Reaction equation

HRID 1627938 reaction equation
CC(C)([O-])C.[K+].[NH2:7][C:8]1[S:12][C:11]2[CH2:13][CH2:14][CH2:15][CH2:16][C:10]=2[C:9]=1[C:17]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)=O.[C:26](OCC)(=[O:34])[CH2:27][CH2:28][C:29]([O:31]CC)=[O:30].Cl>C(O)(C)(C)C.O>[OH:34][C:26]1[N:7]=[C:8]2[S:12][C:11]3[CH2:13][CH2:14][CH2:15][CH2:16][C:10]=3[C:9]2=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=2)[C:27]=1[CH2:28][C:29]([OH:31])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 31249Diethyl SuccinateHCID 754850(2-Amino-4,5,6,7-tetrahydro-1-benzothien-3-yl)(4-methylphenyl)methanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 178423802HCID 178423802, compoundYield 14.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

To a solution of potassium tert-butoxide (0.269 g; 2.4 mmol) in dry tert-butanol (10 mL) under a nitrogen atmosphere at 50° C. were added (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)(p-tolyl)methanone (0.542 g; 2 mmol) and diethyl succinate (0.464 mL; 2.8 mmol). The mixture was heated at reflux for 24 h and then cooled down to room temperature. Water (8 ml) was added and then the reaction mixture was acidified with a solution of hydrochloric acid 1N until pH 1. The aqueous layer was extracted with diisopropylether (3×10 ml) and ethyl acetate (3×10 mL). The organics were combined and the volatiles were removed under reduced pressure. The remaining crude was crystallized from acetic acid to furnish 0.101 g (14%) of the title compound.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 24 h
  3. extractionThe aqueous layer was extracted with diisopropylether (3×10 ml) and ethyl acetate (3×10 mL)
  4. customthe volatiles were removed under reduced pressure
  5. customThe remaining crude was crystallized from acetic acid

Sources & evidence

ORD record
ord-1f84d13be2194769bfb41963a1eed61f
Source dataset
uspto-grants-2014_07
Patent number
US08785638B2

Reaction notes

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