Methyl 3-aminobenzo[b]thiophene-2-carboxylate → HCID 178479161, compound

HRID 1660930Notes

Reaction equation

HRID 1660930 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[C:6]=1[NH2:14])=O.Cl.[Cl:16][C:17]([NH2:19])=[NH:18]>COCCOCCOC>[ClH:16].[NH2:19][C:17]1[N:18]=[C:3]([OH:2])[C:5]2[S:9][C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[C:6]=2[N:14]=1

Participants

4

Reactant 2

HCID 874720Methyl 3-aminobenzo[b]thiophene-2-carboxylateHCID 3084509Chloroformamidinium chloride

Product 1

HCID 178479161HCID 178479161, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
160 °C

Procedure

A suspension of 3-amino-benzo[b]thiophene-2-carboxylic acid methyl ester (1.03 g, 5.0 mmol) and chloroformamidine hydrochloride (800 mg, 7.0 mmol) in diglyme (8 mL) were heated at 160° C. for 1 h. The resulting suspension was cooled to rt and filtered, and the collected solid was suction dried to give the title compound (1.14 g, 90%). 1H NMR (DMSO-d6): 8.06 (d, J=7.9 Hz, 1H), 7.89 (d, J=8.1 Hz, 1H), 7.73-7.47 (m, 2H), 7.45-7.39 (m, 1H), 7.38-7.33 (m, 1H), 7.18 (s, 0.6H), 7.05 (s, 0.6H), 6.92 (s, 0.6H).

Workup

  1. temperatureThe resulting suspension was cooled to rt
  2. filtrationfiltered
  3. customthe collected solid was suction dried

Sources & evidence

ORD record
ord-7154a23b99704913a1e1da73721acd7a
Source dataset
uspto-grants-2011_10
Patent number
US08030321B2

Reaction notes

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