Hydrochloric Acid → HCID 178524203, compound

HRID 884645Notes

Reaction equation

HRID 884645 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([C:12]1[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=1)=O.[NH2:20][C:21]([NH2:23])=[O:22].CC(C)([O-])C.[Na+].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:23][C:21](=[O:22])[N:20]=[C:10]([C:12]2[S:16][C:15]([C:17]([OH:19])=[O:18])=[CH:14][CH:13]=2)[CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 8424963HCID 8424963, compoundHCID 23676156Sodium t-butoxide

Product 1

HCID 178524203HCID 178524203, compoundYield 65.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

(E)-5-(3-(2-chlorophenyl)acryloyl)thiophene-2-carboxylic acid (1.0 g, 3.4 mmol), urea (1.0 g, 16.6 mmol), and sodium t-butoxide (1.6 g, 16.6 mmol) were suspended in 17 mL of 1,4-dioxane. The reaction mixture was stirred overnight at 80° C. After cooling, the suspension was neutralized by the addition of 1M HCl. The precipitate was filtered, washed with water and air dried to give 740 mg of product. 1H NMR (400 MHz, d6-DMSO): δ 7.89 (s, 1H), 7.63 (m, 2H), 7.56 (t, 1H), 7.50 (t, 1H), 7.24 (d, 1H), 7.07 (s, 1H); MS (EI) for C15H9ClN2O3S: 332 (MH+).

Workup

  1. temperatureAfter cooling
  2. filtrationThe precipitate was filtered
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-a7dfce353aa04053a00d9d6b71bfc07a
Source dataset
uspto-grants-2012_08
Patent number
US08242129B2

Reaction notes

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