Hydrochloric Acid → HCID 59180455, compound

HRID 1925709Notes

Reaction equation

HRID 1925709 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9][CH3:10])=[O:8].[CH3:11][C:12]([C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1)([CH3:15])[CH2:13][CH3:14].Cl>ClCCl.C(OCC)(=O)C.N1C=CC=CC=1.ClCCCl>[CH3:15][C:12]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:1][C:2]2[CH:6]=[CH:5][S:4][C:3]=2[C:7]([O:9][CH3:10])=[O:8])(=[O:23])=[O:24])=[CH:20][CH:21]=1)([CH3:11])[CH2:13][CH3:14]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 222819764-(2-Methylbutan-2-yl)benzene-1-sulfonyl chloride

Product 1

HCID 59180455HCID 59180455, compoundYield 48.8%

Reagents, catalysts & solvents 4

HCID 111,2-DichloroethaneSolventHCID 1049PyridineSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-aminothiophene-2-carboxylate (0.184 g; 1.17 mmol) in dichloromethane (2 mL) were added pyridine (0.199 mL; 2.34 mmol) and 4-(1,1-dimethylpropyl)benzenesulfonyl chloride (0.289 g; 1.17 mmol) sequentially. The reaction mixture was stirred for 24 hours at room temperature and then 1,2-dichloroethane (2 mL) and pyridine (1 mL) were added. The reaction mixture was heated at 70° C. for 24 hours, cooled to room temperature, diluted with ethyl acetate and acidified with aqueous hydrochloric acid (2N). The organic layer was separated, concentrated under reduced pressure, and the resulting crude product was purified by chromatography on silica gel eluting with ethyl acetate/hexanes (1:6 v/v) to give the desired product as a white solid (0.21 g).

Workup

  1. temperatureThe reaction mixture was heated at 70° C. for 24 hours
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting crude product was purified by chromatography on silica gel eluting with ethyl acetate/hexanes (1:6 v/v)

Sources & evidence

ORD record
ord-cbb77fa547404af196279bab3ab08580
Source dataset
uspto-grants-2012_05
Patent number
US08178699B2

Reaction notes

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