Formamide → HCID 178494734, compound

HRID 930959Notes

Reaction equation

HRID 930959 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][C:14]([O:19][CH3:20])([CH2:16][O:17][CH3:18])[CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].[CH:21]([NH2:23])=O.C([O-])=O.[NH4+]>>[CH3:20][O:19][C:14]1([CH2:16][O:17][CH3:18])[CH2:13][CH2:12][C:5]2[C:6]3[C:7]([OH:8])=[N:23][CH:21]=[N:1][C:2]=3[S:3][C:4]=2[CH2:15]1

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 118118613HCID 118118613, compound

Product 1

HCID 178494734HCID 178494734, compoundYield 84%

Procedure

A mixture comprising 21.46 g (71.7 mmol) (RS)-ethyl 2-amino-6-methoxy-6-(methoxymethyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (prepared according to intermediate example 16c), 114 mL methanamide and 7.23 g ammonium formate was stirred at 150° C. overnight. The reaction mixture was cooled in an ice bath, the precipitate was filtered off, washed with water and ethanol and dried to give 16.95 g (84%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. filtrationthe precipitate was filtered off
  3. washwashed with water and ethanol
  4. customdried

Sources & evidence

ORD record
ord-f9ed0aade2184e729d490eec3930e068
Source dataset
uspto-grants-2016_03
Patent number
US09296757B2

Reaction notes

Loading…