1-Propanol → N-[2-Nitro-4-(propylsulfanyl)phenyl]acetamide
Reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]#N)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].[CH2:17](O)[CH2:18]C.[OH-].[K+].C(Br)CC>O>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:17][CH3:18])=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2]Participants
Procedure
5 G. of 1-acetamido-2-nitro-4-thiocyanatobenzene in 70 ml. of n-propyl alcohol containing 4.8 g. potassium hydroxide is treated with 2.6 g. n-propylbromide. The mixture is stirred overnight at 15°-20° C., then poured into water, and extracted with chloroform. The dried extracts are stripped under vacuum and the residual red oil is dissolved in 25 ml. of acetic anhydride. A few drops of sulfuric acid are added and the mixture left at 20°-25° C for one hour. Sodium acetate is added and the solvent removed under vacuum. The residue is treated with water and the crude product filtered off. Recrystallization from methanol gives 1-acetamido-2-nitro-4-n-propylthiobenzene. (This intermediate may also be obtained directly by alkylation of 1-acetamido-2-nitro-4-thiocyanatobenzene with n-propylbromide in dimethylformamide in the presence of sodium borohydride.)
Workup
- extractionextracted with chloroform
- dissolutionthe residual red oil is dissolved in 25 ml
- additionA few drops of sulfuric acid are added
- waitthe mixture left at 20°-25° C for one hour
- additionSodium acetate is added
- customthe solvent removed under vacuum
- additionThe residue is treated with water
- filtrationthe crude product filtered off
- customRecrystallization from methanol
Sources & evidence
- ORD record
- ord-f5ab7cfb0c4d4c28a4b35dbfebcc7b3a
- Source dataset
- uspto-grants-1978_03
- Patent number
- US04080461
Reaction notes
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