Formamide → HCID 58905153, compound

HRID 2353821Notes

Reaction equation

HRID 2353821 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:15][CH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12][C:5]=2[C:6]=1[C:7](OCC)=[O:8].[CH:22]([NH2:24])=O>>[O:8]=[C:7]1[NH:24][CH:22]=[N:1][C:2]2[S:3][C:4]3[CH2:15][CH:14]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH2:13][CH2:12][C:5]=3[C:6]1=2

Participants

3

Reactant 2

HCID 713FormamideHCID 17990154HCID 17990154, compound

Product 1

HCID 58905153HCID 58905153, compoundYield 68.4%

Conditions

Temperature
180 °C

Procedure

Formamide (310 mL) was added to ethyl 2-amino-6-(2-ethoxy-2-oxoethyl)-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate (61.2 g, 197 mmol) and the biphasic mixture was heated at 180° C. in an oil bath overnight. The heat was turned off and the reaction solution was allowed to cool. At 60° C., the reaction mixture was seeded and lots of solid quickly precipitated. Upon reaching room temperature the reaction mixture was filtered (very slowly), and rinsed with water (2×150 mL). The damp solid was placed in a vacuum oven and dried at 50° C. overnight to yield a light tan solid (39.3 g, 68.4%). 1H NMR (DMSO-d6) δ 12.31 (s, 1H), 7.99 (s, 1H), 4.09 (q, 2H), 3.06 (m, 1H), 2.87 (m, 1H), 2.75 (m, 1H), 2.40 (m, 3H), 2.19 (m, 1H), 1.89 (m, 1H), 1.47 (m, 1H), 1.19 (t, 3H); LCMS RT=2.40 min, [M+H]+=293.1.

Workup

  1. temperatureto cool
  2. customAt 60° C.
  3. customlots of solid quickly precipitated
  4. customUpon reaching room temperature
  5. filtrationwas filtered (very slowly), and
  6. washrinsed with water (2×150 mL)
  7. customdried at 50° C. overnight

Sources & evidence

ORD record
ord-19c2509da1444714b1b12cac140933b9
Source dataset
uspto-grants-2010_07
Patent number
US07750017B2

Reaction notes

Loading…