Hydrochloric Acid → HCID 67175037, compound

HRID 2383995Notes

Reaction equation

HRID 2383995 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8]([CH2:10]Br)[CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15].[Cl:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:20]=1[CH:26]=C.C(=O)([O-])[O-].[K+].[K+].C(N(CCCC)CCCC)CCC.Cl>CN(C=O)C.C1(P([Pd-2](Cl)(Cl)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:17])[C:4]1[CH:9]=[C:8](/[CH:10]=[CH:26]/[C:20]2[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:19]=2[Cl:18])[CH:7]=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[CH2:14][CH3:15]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7622TributylamineHCID 11430Potassium CarbonateHCID 164682,4-DichlorostyreneHCID 67175327HCID 67175327, compound

Product 1

HCID 67175037HCID 67175037, compound

Reagents, catalysts & solvents 2

HCID 178418903HCID 178418903, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-bromomethyl-2-propionylamino-benzoic acid methyl ester (172 mg, 0.60 mmol), 2,4-dichloro-1-vinyl-benzene (125 mg, 0.72 mmol), potassium carbonate (100 mg, 0.66 mmol), tri-butyl amine (160 μl, 0.66 mmol) and bis(tri-phenyl-phosphino)palladium (II) di-chloride in DMF (3 ml) was heated to 130° C. After 30 minutes, the reaction mixture was allowed to reach room temperature, acidified with 2 M HCl and the resulting precipitate collected by filtration, washed with water and dried under vacuum to give crude 5-[(E)-2-(2,4-dichloro-phenyl)-vinyl]-2-propionylamino-benzoic acid methyl ester. This was hydrolyzed in ethanol (3 mL) and 1.0 M NaOH (3 mL) overnight and then acidified with 1.0 M HCl. The resulting precipitate was collected by filtration, washed with water and dried under vacuum (136 mg, 62% total yield). 1H-NMR (DMSO-d6) δ 1.14 (t, 3H), 2.43 (q, 2H), 7.32 (d, 1H), 7.37 (d, 1H), 7.44 (dd, 1H), 7.63 (d, 1H), 7.87-7.91 (m, 1H), 8.17 (d, 1H), 8.57 (d, 1H), 11.19 (s, 1H), 13.80 (bs, 1H)

Workup

  1. customto reach room temperature
  2. filtrationthe resulting precipitate collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-a624f10b463e47119ae2e9e05071c710
Source dataset
uspto-grants-2012_09
Patent number
US08263658B2

Reaction notes

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