Hydrochloric Acid → 4-(4-Methoxyphenyl)-2-methylaminomethyl-5-(3-pyridyl)-1,3-thiazole
Reaction equation
C[N:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)=[C:5]([C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)[S:4][CH:3]1[CH2:21][NH:22][C:23](=O)C1C=CC=CC=1.Cl.[OH-].[Na+]>>[CH3:14][O:13][C:10]1[CH:9]=[CH:8][C:7]([C:6]2[N:2]=[C:3]([CH2:21][NH:22][CH3:23])[S:4][C:5]=2[C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:12][CH:11]=1Participants
Conditions
- Temperature
- 80 °C
Procedure
To 2-(N-methyl(benzoylaminomethyl)-4-(4-methoxyphenyl)-5-(3-pyridyl)-1,3-thiazole obtained by Example 13 was added 20 ml of 5N-HCl, and the mixture was stirred for 2 hours at 80° C. The reaction solution was left standing for cooling, which was then made alkaline with 2N-NaOH. The alkaline solution was subjected to extraction with ethyl acetate. The extract solution was washed with water, dried and concentrated under reduced pressure, followed by purification by means of a silica-gel column chromatography [eluent: chloroform-methanol (9:1)] to give 2.1 g (yield 91%) of 4-(4-methoxyphenyl)-2-methylaminomethyl-5-(3-pyridyl)-1,3-thiazole. Compounds prepared after the manner described in the above Examples 1-9 are exemplified in Table 1. Melting points are all uncorrected.
Workup
- waitThe reaction solution was left
- temperaturefor cooling
- extractionThe alkaline solution was subjected to extraction with ethyl acetate
- washThe extract solution was washed with water
- customdried
- concentrationconcentrated under reduced pressure
- customfollowed by purification by means of a silica-gel column chromatography [eluent: chloroform-methanol (9:1)]
Sources & evidence
- ORD record
- ord-cf787175057c4cc0baf5e1951641b066
- Source dataset
- uspto-grants-1986_09
- Patent number
- US04612321
Reaction notes
Loading…