Water → HCID 70178178, compound

HRID 842106Notes

Reaction equation

HRID 842106 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][C:11]2[O:12][C:13]3[C:19]([CH2:20][CH2:21][OH:22])=[CH:18][C:17]([Cl:23])=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[O-:29]C#N.[Na+].FC(F)(F)C(O)=O.O>C(Cl)Cl>[C:11](=[O:12])([OH:29])[NH2:15].[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:10][C:11]2[O:12][C:13]3[C:19]([CH2:20][CH2:21][OH:22])=[CH:18][C:17]([Cl:23])=[CH:16][C:14]=3[N:15]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 517096Sodium CyanateHCID 10157910HCID 10157910, compound

Product 1

HCID 70178178HCID 70178178, compoundYield 172.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 2-(3-cyclopentyloxy-4-methoxybenzyl)-5-chloro-7-(2-hydroxyethyl)benzoxazole (0.6 g, 0.0015 mol) and sodium cyanate (0.2 g, 0.0030 mol) was stirred in 4 ml of CH2Cl2 and then trifluoroacetic acid (0.34 g, 0.0030 mol) was added. The mixture was stirred overnight as the initial solid dissolved and a new solid began to form. The next day CH2Cl2 (50 ml) and water (50 ml) were added. The water layer was separated and extracted with 2×50 ml of CH2Cl2. The combined CH2Cl2 layers were washed with 50 ml of water, dried and evaporated to give 0.6 g of white crystalline solid. This material was recrystallized from 6 ml of toluene to give 0.3 g of title compound as white crystals, mp 97-98° C.

Workup

  1. dissolutiondissolved
  2. customto form
  3. customThe water layer was separated
  4. extractionextracted with 2×50 ml of CH2Cl2
  5. washThe combined CH2Cl2 layers were washed with 50 ml of water
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-e0189db1fc804fb89656165eacc7d355
Source dataset
uspto-grants-2002_04
Patent number
US06372770B1

Reaction notes

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