4-Nitrophenol → HCID 14742815, compound

HRID 1651267Notes

Reaction equation

HRID 1651267 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[C:9](/[CH:16]=[CH:17]/[C:18]([OH:20])=[O:19])[S:8][C:7]=2[CH:21]=1.[N+:22]([C:25]1[CH:30]=[CH:29][C:28](O)=[CH:27][CH:26]=1)([O-:24])=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([O:19][C:18](=[O:20])/[CH:17]=[CH:16]/[C:9]2[S:8][C:7]3[CH:21]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=3[C:10]=2[CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[CH:27][CH:26]=1)([O-:24])=[O:23]

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 10868DicyclohexylcarbodiimideHCID 14742804HCID 14742804, compound

Product 1

HCID 14742815HCID 14742815, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

As in Example 113, (E)-3-(6-methoxy-3-pentylbenzo[b]thien-2-yl)-2-propenoic acid (7 g) was reacted with 4-nitrophenol (3.6 g) in dichloromethane (70 mL) in the presence of 1,3-dicyclohexylcarbodiimide (4.8 g). The crude reaction product was crystallized from dichloromethane-2-propanol to give 8.1 g of (E)-3-(6-methoxy-3-pentylbenzo[b]thien-2-yl)-2-propenoic acid 4-nitrophenyl ester, mp 111°-113° C. Anal. Calcd for C23H23NO5S: C, 64.92; H, 5.45; N, 3.29; S, 7.54 Found: C, 64.64; H, 5.35; N, 3.27; S, 7.67

Workup

  1. customThe crude reaction product
  2. customwas crystallized from dichloromethane-2-propanol

Sources & evidence

ORD record
ord-d430fae5bee04a14a8467da41570ed6c
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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