Ammonia → HCID 178508840, compound

HRID 588743Notes

Reaction equation

HRID 588743 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:6]=1[C:7](OCC)=[O:8].Cl.Cl[C:21]([NH2:23])=[NH:22].CS(C)(=O)=O.N>O>[NH2:23][C:21]1[NH:1][C:2]2[S:3][CH:4]=[C:5]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[C:6]=2[C:7](=[O:8])[N:22]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6213Dimethyl SulfoneHCID 613091ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylateHCID 3084509Chloroformamidinium chloride

Product 1

HCID 178508840HCID 178508840, compoundYield 111.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate (400 mg, 1.51 mmol), chloroformamidine hydrochloride (434 mg, 3.78 mmol) and dimethylsulfone (710 mg, 7.55 mmol) was heated at 135° C. for 45 minutes. Water was added and the mixture was cooled down to room temperature. An aqueous ammonia solution was added to adjust the solution to pH 9. The precipitate was filtered off, yielding the title compound (440 mg) as a white powder. δH (300 MHz, DMSO-d6) 10.85 (1H, NH, D2O exchangeable), 7.53 (2H, t), 7.17 (2H, t), 6.92 (1H, s), 6.58 (2H, NH2, D2O exchangeable).

Workup

  1. temperaturethe mixture was cooled down to room temperature
  2. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-62f7a94912e3487880531f299caf3c7f
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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