Formamide → HCID 17990022, compound

HRID 1292952Notes

Reaction equation

HRID 1292952 reaction equation
C([O:3][C:4]([C:6]1[C:7]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][C:8]=2[S:9][C:10]=1[NH2:11])=O)C.[CH:21]([NH2:23])=O>>[O:3]=[C:4]1[NH:23][CH:21]=[N:11][C:10]2[S:9][C:8]3[CH2:12][CH:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:14][CH2:15][C:7]=3[C:6]1=2

Participants

3

Reactant 2

HCID 713FormamideHCID 17990025HCID 17990025, compound

Product 1

HCID 17990022HCID 17990022, compound

Conditions

Temperature
140 °C

Procedure

In a 100 mL round-bottom flask was placed 3.5 g (11.75 mmol, 1 equiv) of 2-amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3,6-dicarboxylic acid diethyl ester in 10 mL of formamide. The flask was equipped with a reflux condenser and heated at 140° C. for 16 h. The mixture was then allowed to cool to rt and a brown solid precipitated from solution. The resulting precipitate was filtered and rinsed with EtOAc (200 mL) and dried in a hi-vac oven for 2 h. After drying 3.25 g (99%) of the desired product as a brown solid was obtained and used without further purification in the next step. LCMS RT=2.80 min; [M+H]+=279.

Workup

  1. customIn a 100 mL round-bottom flask was placed
  2. customThe flask was equipped with a reflux condenser
  3. temperatureto cool to rt
  4. customa brown solid precipitated from solution
  5. filtrationThe resulting precipitate was filtered
  6. washrinsed with EtOAc (200 mL)
  7. customdried in a hi-vac oven for 2 h
  8. dry with materialAfter drying 3.25 g (99%) of the desired product as a brown solid
  9. customwas obtained
  10. customused without further purification in the next step

Sources & evidence

ORD record
ord-04454ab2b7494644835ffce80cc73792
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

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