Hydrochloric Acid → HCID 178418664, compound

HRID 2379396Notes

Reaction equation

HRID 2379396 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.NC1C=CC=CN=1.C([Li])CCC.[S].[Cl-:36].[NH4+].C(OC(NC1[S:51]C=CN=C1)=O)(C)(C)C.Cl>O1CCCC1.C(O)(=O)C>[ClH:36].[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[SH:51]

Participants

11

Reactant 8

HCID 313Hydrochloric AcidHCID 100093-Aminopyridine2×HCID 104392-AminopyridineHCID 25517Ammonium ChlorideHCID 90495Di-tert-butyl dicarbonateHCID 5362487SulfurHCID 675676233-t-Butoxycarbonylamino-4-thia-pyridineHCID 178418339Butyllithium

Product 1

HCID 178418664HCID 178418664, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

In Scheme (3), 3-aminopyridine is acylated with di-t-butyldicarbonate to introduce the t-butoxycarbonyl (t-BOC) protecting group. (It will be appreciated that two other pyridinothiazolothio mercaptans may be prepared by known methodology using other amino pyridine isomers.) The t-BOC protected 3-aminopyridine is then treated with n-butyllithium in tetrahydrofuran followed by elemental sulfur (S8), followed by treatment with saturated ammonium chloride. The resulting 3-t-butoxycarbonylamino-4-thia-pyridine is treated with a mixture of acetic acid and HCl to provide 3-amino-4-mercaptopyridine hydrochloride. The desired 5-pyridinothiazolo thiomercaptan can then be prepared by treating this compound with carbon disulfide under basic conditions.

Sources & evidence

ORD record
ord-2df047e3555f48cea8b9c0ab667fd361
Source dataset
uspto-grants-1994_11
Patent number
US05362722

Reaction notes

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