2-Propenoic acid, 3-(4-aminophenyl)-, hydrochloride → HCID 19594513, compound

HRID 612386Notes

Reaction equation

HRID 612386 reaction equation
[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7](S(Cl)(=O)=O)[CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].Cl.N[C:27]1[CH:37]=[CH:36][C:30]([CH:31]=[CH:32][C:33]([OH:35])=[O:34])=[CH:29][CH:28]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[Cl:1][C:2]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[CH:6]=[C:7]([NH:11][S:12]([C:27]2[CH:37]=[CH:36][C:30](/[CH:31]=[CH:32]/[C:33]([OH:35])=[O:34])=[CH:29][CH:28]=2)(=[O:14])=[O:13])[CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:13])=[O:14]

Participants

6

Reactant 2

HCID 1038662-Propenoic acid, 3-(4-aminophenyl)-, hydrochlorideHCID 23221647HCID 23221647, compound

Product 1

HCID 19594513HCID 19594513, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-(2,4-Dichlorophenoxy)-4-methylsulphonylaminobenzene-sulphonic acid chloride (1.1 g, 2.55 mmol) was dissolved in CH2Cl2 (5 ml) and at 0° C. added dropwise to a solution of 4-aminocinnamic acid hydrochloride (0.65 g, 43.3 mmol) and DMAP (0.44 g, 3.6 mmol) in pyridine (20 ml). The mixture was stirred for 7 hours at 0° C. and then evaporated down. The residue was dried in vacuo and purified by chromatography (silica gel, petroleum ether/ethyl acetate/HOAc 1/1/0.1). Yield: 0.43 g=30% 13C (100 MHz, DMSO-d6) δ 167.68, 149.54, 147.56, 143.23, 139.25, 130.47, 130.33, 130.07, 129.89, 129.42, 129.21, 126.45, 123.19, 122.96, 122.71, 120.18, 118.42, 114.28, 113.74, 41.10

Workup

  1. customevaporated down
  2. customThe residue was dried in vacuo
  3. custompurified by chromatography (silica gel, petroleum ether/ethyl acetate/HOAc 1/1/0.1)

Sources & evidence

ORD record
ord-07c5daf8f0a545f0a19352c05a77da22
Source dataset
uspto-grants-1999_12
Patent number
US06004948

Reaction notes

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