6-[(4-chlorophenyl)sulfanyl]-3-pyridinylamine → HCID 12912740, compound

HRID 444465Notes

Reaction equation

HRID 444465 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl: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>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[C:9]([Cl: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 129127392,6-Dichlorobenzoyl isocyanate

Product 1

HCID 12912740HCID 12912740, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,6-Dichlorobenzoyl isocyanate (2.16 grams; 0.01 mole) and 6-(4-chlorophenylthio)-3-aminopyridine (2.37 grams; 0.01 mole) were mixed in dry ethyl acetate and stirred for 4 hours. The ethyl acetate was removed in vacuo. TLC showed a 3-spot mixture. The reaction mixture was then poured over a silica column with ethyl acetate, and the major spot collected. It was crystallized from ethyl acetate-hexanes, yield 1.5 g., m.p. 160°-162° C.

Workup

  1. customThe ethyl acetate was removed in vacuo
  2. additionThe reaction mixture was then poured over a silica column with ethyl acetate
  3. customthe major spot collected
  4. customIt was crystallized from ethyl acetate-hexanes, yield 1.5 g

Sources & evidence

ORD record
ord-11d3a2f6d2354e08a7cf7140c5cb4767
Source dataset
uspto-grants-1981_04
Patent number
US04264605

Reaction notes

Loading…