Pyridine → Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester

HRID 1921249Notes

Reaction equation

HRID 1921249 reaction equation
[F:1][C:2]1[C:7]2[S:8][CH2:9][CH:10]([NH:11][C:12]([NH:14][CH2:15][CH2:16][OH:17])=[S:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24](Cl)(=[O:26])[CH3:25]>CN(C1C=CN=CC=1)C.C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:7]2[S:8][CH2:9][CH:10]([NH:11][C:12](=[S:13])[NH:14][CH2:15][CH2:16][O:17][C:24](=[O:26])[CH3:25])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 25135276HCID 25135276, compound

Product 1

HCID 25134381Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl esterYield 54.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1-(7-Fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)-3-(2-hydroxy-ethyl)-thiourea (200 mg, 0.73 mmol), pyridine (0.07 mL, 0.88 mmol) and DMAP (20 mg, 0.16 mmol) in THF (5 mL) was added a solution of acetyl chloride (0.06 mL, 0.81 mmol) in THF (2 mL) and the reaction mixture stirred for 16 h. The mixture was diluted with ethyl acetate (20 mL) and extracted with water (4 times). The organic phase was dried over Na2SO4, solvents evaporated and the residue purified by column chromatography to yield Acetic acid 2-[3-(7-fluoro-2,3-dihydro-benzo[b]thiophen-3-yl)thioureido]-ethyl ester (125 mg, 0.40 mmol, 54%).

Workup

  1. extractionextracted with water (4 times)
  2. dry with materialThe organic phase was dried over Na2SO4, solvents
  3. customevaporated
  4. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-216c90bd23c54ded9c113afac5dc9ad8
Source dataset
uspto-grants-2012_05
Patent number
US08173675B2

Reaction notes

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