Dichloromethane → HCID 86592345, compound

HRID 1269573Notes

Reaction equation

HRID 1269573 reaction equation
[C:1]([O:11][C:12]1C=C(Cl)[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=2)=[C:14]([Cl:27])[C:13]=1CC)(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(N([CH2:35][CH3:36])CC)C.[Cl:37][CH:38]([CH3:42])[C:39](Cl)=[O:40].Cl[CH2:44][Cl:45]>>[C:1]([O:11][C:12]1[CH:13]=[C:14]([Cl:27])[C:15]([O:19][C:20]2[CH:21]=[CH:22][C:23]([NH:26][C:39](=[O:40])[CH:38]([Cl:37])[CH3:42])=[CH:24][CH:25]=2)=[C:44]([Cl:45])[C:35]=1[CH3:36])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 1110192-Chloropropionyl chlorideHCID 86592334HCID 86592334, compound

Product 1

HCID 86592345HCID 86592345, compound

Procedure

Stannic chloride (50 mg) was added to a stirred mixture of ethyl(3,5-dichloro-4-[4-aminophenoxy]phenyl) cinnamate (0.10 g), triethylamine (40 mg), dichloromethane (5 mL) and 2-chloropropionyl chloride (50 mg). The reaction mixture was heated at reflux for 16 hours. After concentration and partionating of the residue with ethyl acetate and hydrochloric acid (2 N), 80 mg of methyl(3,5-dichloro-4-[4-(2-chloropropionamido)-phenoxy]phenyl) cinnamate was obtained. The intermediate methyl ester was hydrolyzed using the method described in Example 1(i), to give 60 mg of 3,5-dichloro-4-(4-[2-chloropropionamido]phenoxy)phenylcinnamic acid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 hours
  3. concentrationAfter concentration and partionating of the residue with ethyl acetate and hydrochloric acid (2 N)

Sources & evidence

ORD record
ord-0fb37f0e8f7c4633b0c594e3f7d9f389
Source dataset
uspto-grants-2007_04
Patent number
US07199265B2

Reaction notes

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