Benzenethiol, 2-amino-4-chloro-, hydrochloride (1:1) → HCID 22148788, compound
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.Cl.[NH2:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[SH:29].[Cl:30][C:31]1[CH:36]=[C:35]([N+:37]([O-:39])=[O:38])[CH:34]=[C:33]([Cl:40])[C:32]=1[CH2:41][C:42](O)=O>>[Cl:28][C:26]1[CH:25]=[CH:24][C:23]2[S:29][C:42]([CH2:41][C:32]3[C:33]([Cl:40])=[CH:34][C:35]([N+:37]([O-:39])=[O:38])=[CH:36][C:31]=3[Cl:30])=[N:21][C:22]=2[CH:27]=1Participants
Procedure
By a modification of the procedure of D. L. Boger (J. Org. Chem. 43, 2296-2297 (1978) a solution of P2O5/MeSO3H (Aldrich, 7.5 g, 1:10, w:w) was treated with 2-amino-4-chloro-benzenethiol hydrochloride (example 112, 1.96 g, 10.0 mmol) and (2,6-dichloro-4-nitro-phenyl)-acetic acid (example 110, 2.50 g, 10.0 mmol). The resulting mixture was stirred at room temperature for 1 hour, then heated at 90° C. overnight (15 hours). After cooled to room temperature, the reaction mixture was poured to ice and the resulting mixture was extracted 3× with EtOAc (50 mL). The organic layers were combined and washed twice with a brine solution (100 mL), dried over Na2SO4, and concentrated under vacuum. The crude solid was chromatographed (CH2Cl2) to yield 3.7 g (99%) of compound 114 as a pale yellow solid.
Workup
- temperatureheated at 90° C. overnight (15 hours)
- temperatureAfter cooled to room temperature
- additionthe reaction mixture was poured to ice
- extractionthe resulting mixture was extracted 3× with EtOAc (50 mL)
- washwashed twice with a brine solution (100 mL)
- dry with materialdried over Na2SO4
- concentrationconcentrated under vacuum
- customThe crude solid was chromatographed (CH2Cl2)
Sources & evidence
- ORD record
- ord-36c101079509447d90ebef373faceb4d
- Source dataset
- uspto-grants-2004_08
- Patent number
- US06770648B2
Reaction notes
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