Sodium Hydroxide → HCID 59654755, compound

HRID 1444207Notes

Reaction equation

HRID 1444207 reaction equation
C([O:3][C:4](=[O:29])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]([C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([N:26]([CH3:28])[CH3:27])=[CH:22][CH:21]=3)=[CH:18][CH:19]=2)=[O:14])[CH:7]=1)C.[OH-].[Na+]>O>[CH3:28][N:26]([CH3:27])[C:23]1[CH:22]=[CH:21][C:20]([C:17]2[O:16][C:15]([C:13]([NH:12][C:8]3[CH:7]=[C:6]([CH2:5][C:4]([OH:29])=[O:3])[CH:11]=[CH:10][CH:9]=3)=[O:14])=[CH:19][CH:18]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 59654674HCID 59654674, compound

Product 1

HCID 59654755HCID 59654755, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of (3-[(5-(4-dimethylamino-phenyl)-furan-2-carbonyl)-amino]-phenyl)-acetic acid ethyl ester (13) (0.33 g) in IMS (80 ml) was added a solution of sodium hydroxide (0.65 g) in water (21 ml). The resulting solution was stirred at room temperature for 1 hour then concentrated in vacuo below 40° C. to circa 15 ml volume. Water (50 ml) then acetic acid (1.5 ml) were added and the resulting precipitate filtered, washed with water and triturated with dichloromethane/pentane to yield the title compound (0.26 g; m.p. 187-190° C.).

Workup

  1. concentrationthen concentrated in vacuo below 40° C. to circa 15 ml volume
  2. additionWater (50 ml) then acetic acid (1.5 ml) were added
  3. filtrationthe resulting precipitate filtered
  4. washwashed with water
  5. customtriturated with dichloromethane/pentane

Sources & evidence

ORD record
ord-88b581ba15e7427cb4f3f397500cf9e1
Source dataset
uspto-grants-2010_02
Patent number
US07662839B2

Reaction notes

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