Water → HCID 14822218, compound

HRID 1085486Notes

Reaction equation

HRID 1085486 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][C:7]=1[Cl:8].[C:13]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)(N1C=CN=C1)=O.O.[CH2:26]1[CH2:30]O[CH2:28][CH2:27]1>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:22]([CH3:21])[C@H:23]2[C@H:24]([N:20]3[CH2:13][CH2:9][CH2:4][CH2:5]3)[CH2:6][C:7]3[C:27](=[CH:26][CH:30]=[CH:3][CH:2]=3)[CH2:28]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 798743,4-Dichlorophenylacetic acid

Product 1

HCID 14822218HCID 14822218, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,4-Dichlorophenylacetic acid (1.05 g) and carbonyldiimidazole (856 mg) were dissolved in dry THF (20 ml). This solution was cannulated into a stirred suspension of the above product (1.0 g) in methylene chloride (20 ml) at 0°. The mixture was allowed to warm to room temperature and stirred overnight. Water (50 ml) and methylene chloride (100 ml) were added and the organic layer was separated, washed with brine, dried, and evaporated to give a crude product which was chromatographed (silica gel; CH2Cl2 :CH3OH=40:1) to yield the pure free base of the title compound (1.2 g). Its naphthalenesulfonate was recrystallized from ethyl acetate: 2-propanol; m.p. 161°-164°.

Workup

  1. customthe organic layer was separated
  2. washwashed with brine
  3. customdried
  4. customevaporated
  5. customto give a crude product which
  6. customwas chromatographed (silica gel; CH2Cl2 :CH3OH=40:1)

Sources & evidence

ORD record
ord-548166faacbb4840b790e6dba50e453f
Source dataset
uspto-grants-1991_04
Patent number
US05010085

Reaction notes

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