Tetrahydrofuran → HCID 86609906, compound

HRID 732930Notes

Reaction equation

HRID 732930 reaction equation
[NH2:1][C:2]1[N:6]([CH2:7][CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([OH:18])=[O:17].[C:19]([N:27]=[C:28]=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O1CC[CH2:32][CH2:31]1>>[C:19]([NH:27][C:28]([NH:1][C:2]1[N:6]([CH2:7][CH:8]([OH:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:31][CH3:32])=[O:17])=[S:29])(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 68284Benzoyl isothiocyanateHCID 108794365-amino-1-(2-hydroxy-2-phenylethyl)-1H-pyrazole-4-carboxylic acid

Product 1

HCID 86609906HCID 86609906, compoundYield 93%

Procedure

A suspension of 5 (2.7 g, 10 mmol) and benzoyl isothiocyanate (1.7 g, 11 mmol) in anhydrous tetrahydrofuran (THF) (20 mL) was refluxed for 12 h. The solvent was evaporated under reduced pressure; the oil residue crystallized adding diethyl ether (30 mL) to afford the pure product 6 (4.07 g, 93%) as a white solid; mp 171-172° C. 1H NMR: δ 1.29 (t, J=7.0, 3H, CH3), 3.97-4.20 (m, 5H, 2CH2+OH, 1H disappears with D2O), 4.58-4.68 (m, 1H, CHO), 7.05-7.98 (m, 10H Ar), 8.02 (s, 1H, H-3), 8.70 (s, 1H, NH, disappears with D2O), 12.05 (s, 1H, NH, disappears with D2O). IR cm−1: 3221 (NH), 3190-2940 (OH), 1708 and 1671 (2 CO). Anal. (C22H22N4O4S) C, H, N, S.

Workup

  1. temperaturewas refluxed for 12 h
  2. customThe solvent was evaporated under reduced pressure
  3. customthe oil residue crystallized
  4. additionadding diethyl ether (30 mL)

Sources & evidence

ORD record
ord-ea2337fad70e4ea492ddfc9a7c76667a
Source dataset
uspto-grants-2009_09
Patent number
US07589086B2

Reaction notes

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