Ammonium Chloride → 4-[(4-tert-Butylphenyl)sulfanyl]-3-chloroaniline

HRID 1428818Notes

Reaction equation

HRID 1428818 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][C:13]=2[Cl:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>CC(C)=O.CCOC(C)=O.[Zn]>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[CH:14][C:13]=2[Cl:21])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 68486166HCID 68486166, compound

Product 1

HCID 433307174-[(4-tert-Butylphenyl)sulfanyl]-3-chloroaniline

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-tert-butyl-phenylsulfanyl)-2-chloro-4-nitro-benzene was dissolved in acetone (15 mL), then saturated aqueous NH4Cl (5 mL) was added and the mixture was cooled to 0° C. Solid zinc powder (3.7 g, 56 mmol) was added in portions over 10 min with rapid stirring. The mixture was allowed to warm to rt and was stirred 3 h. The mixture was diluted with EtOAc (250 mL), dried, and filtered through Celite®. Removal of solvent gave a yellow residue, which was used without further purification. MS (ESI): mass calcd. for C16H18ClNS, 291.1; m/z found 292.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 7.33-7.21 (m, 3H), 6.95 (d, J=8.5, 2H), 6.77 (d, J=2.4, 1H), 6.55 (dd, J=8.4, 2.4, 1H), 5.80 (s, 2H), 1.22 (s, 9H).

Workup

  1. temperatureto warm to rt
  2. customdried
  3. filtrationfiltered through Celite®
  4. customRemoval of solvent
  5. customgave a yellow residue, which
  6. customwas used without further purification

Sources & evidence

ORD record
ord-a5b5aaf78b91402a86b085a698a4d83c
Source dataset
uspto-grants-2015_01
Patent number
US08937078B2

Reaction notes

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