Formamide → HCID 59380494, compound

HRID 2353831Notes

Reaction equation

HRID 2353831 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:15]=[C:14]([Br:16])[CH:13]=[CH:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].[CH:17]([NH2:19])=O.C([O-])=O.[NH4+]>>[Br:16][C:14]1[CH:13]=[CH:12][C:5]2[C:6]3[C:7](=[O:8])[NH:19][CH:17]=[N:1][C:2]=3[S:3][C:4]=2[CH:15]=1

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 18422163Ethyl 6-bromo-2-aminobenzo[b]thiophene-3-carboxylate

Product 1

HCID 59380494HCID 59380494, compound

Procedure

Ethyl 2-amino-6-bromo-1-benzothiophene-3-carboxylate (9.0 g, 27 mmol), formamide (85 mL) and ammonium formate (2.7 g, 43 mmol) were heated in an oil bath at 135° C. overnight. The next morning the reaction mixture was a pastel blue slurry. The reaction mixture was allowed to cool to room temperature and was then filtered. The solid was washed with water, dried by filtration, and finally dried in a vacuum oven overnight at 45° C. to yield a light blue solid (7.8 g, quantitative). 1H NMR (DMSO-d6) δ 12.9 (br, 1H), 8.37 (s, 1H), 8.35 (d, 1H), 8.31 (s, 1H), 7.69 (d, 1H); LCMS RT=3.08 min, [M+H]+=281.1.

Workup

  1. filtrationwas then filtered
  2. washThe solid was washed with water
  3. customdried by filtration
  4. customfinally dried in a vacuum oven overnight at 45° C.
  5. customto yield a light blue solid (7.8 g, quantitative)

Sources & evidence

ORD record
ord-090981f0e0924c30a5e058ba3f545717
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

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