Ethanolamine → Benzamide, N-(2-hydroxyethyl)-4-(phenylmethoxy)-

HRID 1419936Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:18](C1NC=CN=1)([C:20]1[NH:21]C=CN=1)=[O:19].C(CN)O>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:21][CH2:20][CH2:18][OH:19])=[O:15])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 4-benzyloxy benzoic acid (20 g, 87.6 mmol), 1,1,-carbonyl-diimidazole (14.9 g, 91.8 mmol) and DMF (80 ml) was stirred at 50° C. for 1 h. The solution is cooled to 0° C., and ethanolamine (25% in water, 81.2 g) is added. After 45 min., the precipitate was filtered to give 4-benzyloxy-N-(2-hydroxy-ethyl)-benzamide (22.49 g, 94.5%) as a white solid. MS: me/e=271 (M)+.

Workup

filtrationthe precipitate was filtered

Sources & evidence

ORD record: ord-6fae201f97de4032bc83c2c6c96c1ad5
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05889026

Reaction notes

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