Hydrochloric Acid → HCID 70277266, compound

HRID 1604289

Reaction equation

HRID 1604289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([CH:13]=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH2:15][N:16]1[CH2:20][CH:19]([CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[O:18][C:17]1=[O:28].Cl>>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([CH:13]=[N:15][N:16]3[CH2:20][CH:19]([CH2:21][N:22]4[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]4)[O:18][C:17]3=[O:28])=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6761845-(4-Chlorophenyl)-2-furaldehydeHCID 15434827HCID 15434827, compound

Product 1

HCID 70277266HCID 70277266, compound

Procedure

5-(4-Chlorophenyl)-2-furancarboxaldehyde [prepared as described in U.S. Pat. No. 4,882,354, to Huang et al. (assigned to Norwich Eaton Pharmaceuticals, Inc.,) issued Nov. 21, 1984; see cols. 7 & 8, hereby incorporated by reference] (3.92 g, 19.0 mmole) and 3-amino-5-(1-piperidinyl)methyl-2-oxazolidinone (3.78 g, 19.0 mole)[(prepared as described in U.S. Pat. No. 2,802,002 to Gever, (assigned to Norwich Eaton Pharmaceuticals, Inc. issued Aug. 6, 1957, see Example I, Part A, hereby incorporated by reference herein) in 150 ml of alcohol is treated with 3 ml of concentrated hydrochloric acid (pH ca. 3). The reaction mixture is stirred and heated at reflux for 2.5 hours. The mixture is chilled and filtered to give crude 3-[[[5-(4-chlorophenyl)-2-furanyl]methylene]amino]-5-(1-piperidinylmethyl)-2-oxazolidinone hydrochloride, which is purified by one recrystallization from nitromethane (activated charcoal) yielding 3.2 g.

Workup

  1. temperatureheated
  2. temperatureat reflux for 2.5 hours
  3. temperatureThe mixture is chilled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-951faccfe3e346afa14e1b4b803313b1
Source dataset
uspto-grants-1999_11
Patent number
US05994354

Linked notes

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