Ethanolamine → HCID 19038599, compound

HRID 363701Notes

Reaction equation

HRID 363701 reaction equation
C(CN)O.[OH:5][CH2:6][CH2:7][NH:8][C:9](=O)[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH2:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:14][CH:13]=1.S(Cl)(Cl)=O.O.Cl>CCOC(C)=O>[C:28]1([C:21]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:20][CH2:19][O:18][C:15]2[CH:14]=[CH:13][C:12]([CH2:11][CH2:10][C:9]3[O:5][CH2:6][CH2:7][N:8]=3)=[CH:17][CH:16]=2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 700EthanolamineHCID 24386Thionyl ChlorideHCID 21885828Hydrate;hydrochlorideHCID 54529025HCID 54529025, compound

Product 1

HCID 19038599HCID 19038599, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

By the method of example 25, ethanolamine was converted to N-(2-hydroxyethyl)-3-[4-(3,3,3-triphenylpropoxy)-phenyl]propionamide. To this amide (400 mg; 0.84 mmol) in EtOAc (15 mL), was added dropwise over 5 minutes thionyl chloride (0.20 mL, 2.74 mmol) in EtOAc (2 mL) under a nitrogen atmosphere at room temperature. After stirring overnight, the precipitate was collected and washed with EtOAc to give the title compound (354.1 mg; 85% yield) as the hydrochloride monohydrate, a white powder. mp=130°-131° C. 1H NMR δ 7.19-7.34 (m, 15H), 7.02 (d, J=8.6 Hz, 2H), 6.62 (d, J=8.6 Hz, 2H), 3.70 (t, J=7.7 Hz, 2H), 3.53 (br s, 4H), 3.12 (t, J=7.7 Hz, 2H), 2.87 (t, J=7.5 Hz, 2H), 2.43 (t, J=7.5 Hz, 2H). IR 2954, 1513, 1245 cm-1. MS 462 (MH+), 243. Anal. calcd. for C32H31NO2 ·HCl·H2O: C, 74.48; H, 6.48; N, 2.71. Found: C, 74.26; H, 6.32; N, 2.70.

Workup

  1. customthe precipitate was collected
  2. washwashed with EtOAc

Sources & evidence

ORD record
ord-7703d6a7f338429a928637eada7253c7
Source dataset
uspto-grants-1999_02
Patent number
US05874436

Reaction notes

Loading…