Ammonia → HCID 19855557, compound
Reaction equation
S(Cl)(Cl)=O.[ClH:5].[CH3:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:8]=1NCC(O)C.O.[NH3:20].[CH:21]1[CH:26]=CC=C[CH:22]=1>>[CH3:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH3:6])[C:8]=1[CH:22]([NH2:20])[CH:21]([Cl:5])[CH3:26]Participants
Procedure
A solution of 18.0 ml (29.7 g, 0.25 moles) of thionyl chloride in 50 ml of dry benzene is added dropwise, within 0.5 hours, to a suspension of 43.15 g (0.20 moles) of 1-(2,6-dimethylphenyl-amino)-2-propanol hydrochloride in 400 ml of dry benzene. The addition is performed at room temperature under nitrogen atmosphere. The reaction mixture is boiled for 3 hours, then the resulting solution is cooled to room temperature, and 50 ml of water are added dropwise to the mixture at a temperature not exceeding 20° C. Concentrated aqueous ammonia is added then dropwise to the mixture to adjust the pH of the aqueous phase to 9. The phases are separated from each other, and the aqueous phase is extracted twice with 100 ml of benzene, each. The benzene solutions are combined, washed thrice with 100 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated. The oily residue is distilled under reduced pressure. 27.6 g (70%) of 1-(2,6-dimethylphenyl)-amino-2-chloro-propane are obtained; b.p.: 99°-100° C./53.3 Pa.
Workup
- additionThe addition
- customis performed at room temperature under nitrogen atmosphere
- customexceeding 20° C
- customThe phases are separated from each other, and the aqueous phase
- extractionis extracted twice with 100 ml of benzene
- washwashed thrice with 100 ml of water
- dry with materialeach, dried over anhydrous magnesium sulfate
- customthe solvent is evaporated
- distillationThe oily residue is distilled under reduced pressure
Sources & evidence
- ORD record
- ord-8e389ed0c9d649edb69de691b001e81e
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04922021
Reaction notes
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