Ammonia → HCID 178435038, compound

HRID 588744Notes

Reaction equation

HRID 588744 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:18])=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[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][C:4]([CH3:18])=[C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:6]=2[C:7](=[O:8])[N:22]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6213Dimethyl SulfoneHCID 693902ethyl 2-amino-5-methyl-4-phenylthiophene-3-carboxylateHCID 3084509Chloroformamidinium chloride

Product 1

HCID 178435038HCID 178435038, compoundYield 94.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl 2-amino-5-methyl-4-phenylthiophene-3-carboxylate (1 g, 3.8 mmol), chloroformamidine hydrochloride (1.1 g, 9.6 mmol) and dimethylsulfone (1.798 g, 19.1 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 (920 mg) as a yellowish powder. 13C NMR δ (75 MHz, DMSO-d6) 166.50, 157.60, 153.02, 135.16, 133.40, 130.30 (2C), 127.35 (2C), 126.79, 124.22, 113.80, 13.33. MS (m/z) 258 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-201ee775031c485ab97ce97aec6be776
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Reaction notes

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