Benzyl mercaptan → HCID 18963786, compound

HRID 2226855Notes

Reaction equation

HRID 2226855 reaction equation
[CH2:1]([SH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:10]1[C:11]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:12]=2[S:13][C:14]=1[C:15]([NH2:17])=[O:16].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C=O)C.C(OCC)(=O)C>[CH3:23][O:22][C:20]1[CH:19]=[CH:18][C:12]2[S:13][C:14]([C:15]([NH2:17])=[O:16])=[C:10]([S:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:11]=2[CH:21]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 106815953-Chloro-5-methoxybenzo[b]thiophene-2-carboxamideHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18963786HCID 18963786, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Benzylmercaptan (134 μL, 1.14 mmol) is added to a suspension of 3-chloro-5-methoxybenzo[b]thiophene-2-carboxamide (250 mg, 1.03 mmol) in 2 mL of DMF. Diazabicycloundecene (DBU) (170 μL, 1.14 mmol) is added and the mixture is warmed to 50° C. After 1 hour, the reaction mixture is allowed to cool and then is diluted with ethyl acetate and washed with 1N NaOH, 1N HCl, water, and brine. The organic layer is dried over MgSO4. Filtration followed by concentration in vacuo and recrystallization from ethyl acetate: hexane gives 5-methoxy-3-[(phenylmethyl)thio]benzo[b]thiophene-2-carboxamide in 63% yield; mp=151°-153° C.

Workup

  1. temperatureto cool
  2. washwashed with 1N NaOH, 1N HCl, water, and brine
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationFiltration
  5. concentrationfollowed by concentration in vacuo and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2a6db4ebf37f46ea9f3f692c283d5968
Source dataset
uspto-grants-1994_09
Patent number
US05350748

Reaction notes

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