Ammonia → HCID 178431879, compound

HRID 588746

Reaction equation

HRID 588746 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:12])[C:6]=1[C:7](OCC)=[O:8].Cl.Cl[C:15]([NH2:17])=[NH:16].CS(C)(=O)=O.N>O>[NH2:17][C:15]1[NH:1][C:2]2[S:3][CH:4]=[C:5]([CH3:12])[C:6]=2[C:7](=[O:8])[N:16]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6213Dimethyl SulfoneHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylateHCID 3084509Chloroformamidinium chloride

Product 1

HCID 178431879HCID 178431879, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of ethyl 2-amino-4-methylthiophene-3-carboxylate (2.0 g, 11.7 mmol), chloroformamidine hydrochloride (3.357 g, 29.0 mmol) and dimethylsulfone (5.489 g, 58.4 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 (1.863 g) as a white powder. 13C NMR δ (75 MHz, DMSO-d6) 168.98, 159.12, 153.21, 133.26, 114.37, 110.81, 16.35. MS (m/z) 182 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-c1695a9815aa42c2b10daecd926f3082
Source dataset
uspto-grants-2016_01
Patent number
US09227984B2

Linked notes

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