Ethanolamine → Win 52035

HRID 1905474Notes

Reaction equation

HRID 1905474 reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:17][N:16]=[C:15]([CH3:18])[CH:14]=2)=[CH:5][CH:4]=1)#[N:2].[OH:21][CH2:22][CH2:23]N>>[O:21]1[CH2:22][CH2:23][N:2]=[C:1]1[C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:17][N:16]=[C:15]([CH3:18])[CH:14]=2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 700EthanolamineHCID 52712115-[5-(4-Cyanophenoxy)pentyl]-3-methylisoxazole

Product 1

HCID 1786Win 52035Yield 68%

Procedure

5-{5-[4-(4,5-Dihydro-2-oxazolyl)phenoxy]pentyl}-3-methylisoxazole [IX; R=CH3, R1, R2, R3, R4, R5 and R6 =H, Y=(CH2)5, oxazole at 4-position] was prepared by conversion of 5-[5-(4-cyanophenoxy)pentyl]-3-methylisoxazole to the corresponding ethyl imino-ester hydrochloride (m.p. 120°-121° C.) and reaction of the latter with 2-hydroxyethylamine in accordance with the proceudre of Example 1, part (c). The product was obtained in 68% yield as a colorless solid, m.p. 87°-88° C.; monomethanesulfonate salt, m.p. 124°-125° C. The free base was obtained as a colorless solid, m.p. 102°-103.5° C.

Workup

  1. customThe product was obtained in 68% yield as a colorless solid, m.p. 87°-88° C.
  2. customThe free base was obtained as a colorless solid, m.p. 102°-103.5° C.

Sources & evidence

ORD record
ord-350480aff9864386a4bb2349227734e3
Source dataset
uspto-grants-1989_06
Patent number
US04843087

Reaction notes

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