2-Chloropropionyl chloride → HCID 86592338, compound

HRID 1269568Notes

Reaction equation

[C:1]([O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH2:26])=[C:22]([Br:27])[CH:21]=2)=[C:14]([Cl:28])[C:13]=1[CH2:29][CH3:30])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Cl:31][CH:32]([CH3:36])[C:33](Cl)=[O:34]>>[C:1]([O:11][C:12]1[CH:17]=[C:16]([Cl:18])[C:15]([O:19][C:20]2[CH:25]=[CH:24][C:23]([NH:26][C:33](=[O:34])[CH:32]([Cl:31])[CH3:36])=[C:22]([Br:27])[CH:21]=2)=[C:14]([Cl:28])[C:13]=1[CH2:29][CH3:30])(=[O:10])[CH:2]=[CH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 1110192-Chloropropionyl chloride

HCID 86592337HCID 86592337, compound

Product 1

HCID 86592338HCID 86592338, compoundYield 83%

Procedure

Ethyl(3,5-dichloro-4-[4-amino-3-bromophenoxy]phenyl) cinnamate (70 mg) was coupled with 2-chloropropionyl chloride (30 mg), using the method described in Example 1(h). After purification on column (silica gel, ethyl acetate/petrolium ether, 1:9), 45 mg (83%) of ethyl(3,5-dichloro-4-[3-bromo-4-(2-chloropropionamido)phenoxy]phenyl) cinnamate was obtained. A part of the ethyl ester (50 mg) was hydrolysed using the method described in Example 1(i), to give 40 mg (84%) of 3,5-dichloro-4-(3-bromo-4-[2-chloropropionamido]-phenoxy)phenylcinnamic acid.

Workup

customAfter purification on column (silica gel, ethyl acetate/petrolium ether, 1:9)

Sources & evidence

ORD record: ord-76a923a2811442cab74e902c8e046338
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07199265B2

Reaction notes

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