2-Aminophenol → N-(1,3-benzothiazol-2-yl)-1,3-benzoxazol-2-amine
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].[OH-].[Na+].C[SH-][C:13]([SH-]C)=[N:14][C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1>CN(C=O)C.O>[S:16]1[C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=[C:15]1[NH:14][C:13]1[O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=1Participants
Procedure
2-aminophenol (21.8 g (0.20 mol)) was dissolved in 944 g of DMF, thereto was added 40 mL of 5 mol/L aqueous sodium hydroxide solution (equivalent to 0.20 mol of sodium hydroxide), the resulting mixture was stirred at room temperature for 30 minutes, and then thereto was added a solution obtained by dissolving 50.9 g (0.20 mol) of the obtained S,S′-dimethyl-N-(2-benzothiazolyl)carbonimidodithioate in 1416 g of DMF. The resulting mixture was then heated to 153° C., refluxed under a nitrogen atmosphere for 6 hours, and then cooled to room temperature, and the reaction liquid was added dropwise in 2000 g of water. A precipitate was filtered off, washed with water, and dried to obtain 30.0 g of 2-(2-benzothiazolylamino)benzoxazole (L5: see Table 1 below). The yield was 56.1% based on 2-aminophenol.
Workup
- additionwas added a solution
- customobtained
- temperatureThe resulting mixture was then heated to 153° C.
- temperaturerefluxed under a nitrogen atmosphere for 6 hours
- temperaturecooled to room temperature
- customthe reaction liquid
- filtrationA precipitate was filtered off
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-8f8076750de14940bbb0b3f7c0e4da49
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08540904B2
Reaction notes
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