Chloromethyl acetate → 3-(2-Aminoethylamino)benzo[b]thiophene-2-carboxylic acid methyl ester hydrochloride

HRID 864960Notes

Reaction equation

HRID 864960 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[SH:12].[C:13]([O:16][CH2:17][Cl:18])(=[O:15])[CH3:14]>CO>[ClH:18].[CH3:17][O:16][C:13]([C:14]1[S:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:2]=1[NH:3][CH2:4][CH2:5][NH2:1])=[O:15]

Participants

4

Reactant 2

HCID 69366Chloromethyl acetateHCID 14773612-(4,5-dihydro-1H-imidazol-2-yl)benzenethiol

Product 1

HCID 698533193-(2-Aminoethylamino)benzo[b]thiophene-2-carboxylic acid methyl ester hydrochlorideYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(4,5-dihydro-1H-imidazol-2-yl)benzenethiol (1.00 g, 5.62 mmol) [Hegen, H., Fleig, H. Justus Liebigs Ann. Chem. 11:1994 (1975)] and chloromethyl acetate (610 mg, 5.62 mmol) in 15 mL of methanol is heated at reflux for 90 minutes. The reaction is cooled to room temperature and filtered. The filtrate is concentrated to dryness and the residue dissolved in hot chloroform. After several hours the resulting precipitate is collected and dried. The mother liquor affords a second crop of crystals giving 3-(2-aminoethylamino)benzo[b]thiophene-2-carboxylic acid methyl ester hydrochloride in an overall yield of 61%, mp 219°-220° C.

Workup

  1. temperatureat reflux for 90 minutes
  2. filtrationfiltered
  3. concentrationThe filtrate is concentrated to dryness
  4. dissolutionthe residue dissolved in hot chloroform
  5. customAfter several hours the resulting precipitate is collected
  6. customdried
  7. customThe mother liquor affords a second crop of crystals

Sources & evidence

ORD record
ord-ea3c82e5bad8407b8e12f83866dda335
Source dataset
uspto-grants-1996_10
Patent number
US05565446

Reaction notes

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