Ammonium Chloride → 5-[(4-Chlorophenyl)sulfanyl]pyridin-2-amine

HRID 444471Notes

Reaction equation

HRID 444471 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:6][N:5]=1)([O-])=O.[Cl-].[NH4+]>[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10][C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 12912741HCID 12912741, compound

Product 1

HCID 129127435-[(4-Chlorophenyl)sulfanyl]pyridin-2-amine

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Procedure

2-Nitro-5-(4-chlorophenylthio)pyridine (10.5 grams), ammonium chloride (50.0 grams), and powdered iron (30.0 grams) were reacted in the same procedures reported in Example 3. The reaction mixture was filtered hot solvents were removed. The product was extracted with ethyl acetate, washed with water, the ethyl acetate removed, and the product crystallized from ethyl acetate-hexanes, yield 4.5 grams, m.p. 157°-159° C.

Workup

  1. filtrationThe reaction mixture was filtered hot solvents
  2. customwere removed
  3. extractionThe product was extracted with ethyl acetate
  4. washwashed with water
  5. customthe ethyl acetate removed
  6. customthe product crystallized from ethyl acetate-hexanes, yield 4.5 grams, m.p. 157°-159° C.

Sources & evidence

ORD record
ord-2f8ea697d9d74a2d80506e9342fd4fca
Source dataset
uspto-grants-1981_04
Patent number
US04264605

Reaction notes

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