Calcium Carbonate → N-(4-chlorophenyl)-2-[((5-hydroxymethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

HRID 844192Notes

Reaction equation

HRID 844192 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([C:20]2[S:21][C:22]([CH2:26]Br)=[CH:23][C:24]=2[Cl:25])=[O:19])=[CH:4][CH:3]=1.C([O-])([O-])=[O:30].[Ca+2]>O1CCOCC1.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[NH:17][C:18]([C:20]2[S:21][C:22]([CH2:26][OH:30])=[CH:23][C:24]=2[Cl:25])=[O:19])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10112Calcium CarbonateHCID 18376771N-(4-chlorophenyl)-2-[((5-(bromomethyl)-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide

Product 1

HCID 18376684N-(4-chlorophenyl)-2-[((5-hydroxymethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamideYield 56.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of N-(4-chlorophenyl)-2-[((5-bromomethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide (0.3 g, 0.58 mmol) in dioxane (10 mL) and water (2 mL) was added CaCO3 (0.29 g, 2.89 mmol). The resulting turbid solution was heated to reflux for 64 hours, and then cooled to ambient temperature. The reaction mixture was concentrated to remove dioxane and purified by flash chromatography on silica followed by precipitation from CH2Cl2 and hexane to afford 0.15 g of N-(4-chlorophenyl)-2-[((5-hydroxymethyl-3-chlorothiophen-2-yl)carbonyl)amino]-5-chlorobenzamide, as a yellow solid; NMR (DMSO-d6/TFA) 11.1 (s, 1), 10.7 (s, 1), 8.4 (d, 1), 7.9 (s, 1), 7.7 (d, 2), 7.5 (d, 1), 7.3 (d, 2), 7.0 (s, 1), 4.6(s, 2) ppm.

Workup

  1. temperatureThe resulting turbid solution was heated
  2. temperatureto reflux for 64 hours
  3. concentrationThe reaction mixture was concentrated
  4. customto remove dioxane
  5. custompurified by flash chromatography on silica
  6. customfollowed by precipitation from CH2Cl2 and hexane

Sources & evidence

ORD record
ord-f3c2390837a2471eabc952b0c0017496
Source dataset
uspto-grants-2002_04
Patent number
US06380221B1

Reaction notes

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