Acetyl chloride → 2-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl ester

HRID 1594227Notes

Reaction equation

HRID 1594227 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH2:14][CH2:13][CH2:12][C:5]=2[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[C:16](Cl)(=[O:18])[CH3:17]>C1COCC1.CN(C)C1C=CN=CC=1.[Cl-].[Na+].O>[CH2:10]([O:9][C:7]([C:6]1[C:5]2[CH2:12][CH2:13][CH2:14][CH2:15][C:4]=2[S:3][C:2]=1[NH:1][C:16](=[O:18])[CH3:17])=[O:8])[CH3:11]

Participants

6

Reactant 2

HCID 6367Acetyl chlorideHCID 78262Ethyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Product 1

HCID 986822-Acetylamino-4,5,6,7-tetrahydrobenzothiophene-3-carboxylic acid ethyl esterYield 96.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of ethyl 2-amino-4, 5, 6, 7-tetrahydrobenzothiophene-3-carboxylate (16 g, 71.1 mmol) in THF (100 mL) was added 4-(dimethylamino)pyridine (434 mg, 3.55 mmol) and acetyl chloride (6.1 mL, 85.3 mmol). After stirring for 2 h at room temperature, the solution was diluted with brine solution (500 mL) and extracted with ethyl acetate (500 mL, 3×). The combined organic phases were dried over MgSO4, filtered, and concentrated to provide the title compound (18.3 g, 96%) as a light yellow solid: MS (ES) m/z 268 (M+H)+.

Workup

  1. extractionextracted with ethyl acetate (500 mL, 3×)
  2. dry with materialThe combined organic phases were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-269027c67f7a4062abd10f8b2866cf5b
Source dataset
uspto-grants-2007_11
Patent number
US07300952B2

Reaction notes

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