6-[(4-chlorophenyl)sulfanyl]-3-pyridinylamine → HCID 23463887, compound

HRID 444468Notes

Reaction equation

HRID 444468 reaction equation
[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([N:6]=[C:7]=[O:8])=[O:5].[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[N:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=2)=[CH:17][CH:16]=1>C(OCC)(=O)C>[CH3:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([NH:6][C:7]([NH:28][C:25]1[CH:26]=[N:27][C:22]([S:21][C:18]2[CH:19]=[CH:20][C:15]([Cl:14])=[CH:16][CH:17]=2)=[CH:23][CH:24]=1)=[O:8])=[O:5]

Participants

4

Reactant 2

HCID 28001276-[(4-chlorophenyl)sulfanyl]-3-pyridinylamineHCID 201325392,6-Dimethylbenzoyl isocyanate

Product 1

HCID 23463887HCID 23463887, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,6-Dimethylbenzoyl isocyanate (1.61 grams; 0.01 mole) and 6-(4-chlorophenylthio)-3-aminopyridine (2.36 grams; 0.01 mole) were mixed in 50 ml. of ethyl acetate and stirred at room temperature for 12 hours. Solvent was removed in vacuo. TLC showed four spots. The mixture was passed over a column of silica gel with a 1:1 mixture of toluene-ethyl acetate and the product (Rf ≅0.7) separated and crystallized from ethyl acetate-hexanes, yield 1.1 grams, m.p. 159°-160° C.

Workup

  1. customSolvent was removed in vacuo
  2. additionThe mixture was passed over a column of silica gel with a 1:1 mixture of toluene-ethyl acetate
  3. customthe product (Rf ≅0.7) separated
  4. customcrystallized from ethyl acetate-hexanes, yield 1.1 grams, m.p. 159°-160° C.

Sources & evidence

ORD record
ord-5effab1027164544948dda82d4229120
Source dataset
uspto-grants-1981_04
Patent number
US04264605

Reaction notes

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