Hydrochloric Acid → Methyl 2-(4-(naphthalen-1-yl)-1,2,3-thiadiazol-5-ylthio)acetate

HRID 386397Notes

Reaction equation

HRID 386397 reaction equation
[OH-].[Na+].N1([C:12]2[S:16][N:15]=[N:14][C:13]=2[C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][CH:18]=2)C2C=CC=CC=2N=N1.C[CH:28]([SH:32])[C:29]([O-:31])=[O:30].Cl.[CH3:34]N(C=O)C>>[C:17]1([C:13]2[N:14]=[N:15][S:16][C:12]=2[S:32][CH2:28][C:29]([O:31][CH3:34])=[O:30])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 156077362-MercaptopropionateHCID 668209545-(1H-benzo[d][1,2,3]triazol-1-yl)-4-(naphthalen-1-yl)-1,2,3-thiadiazole

Product 1

HCID 66820853Methyl 2-(4-(naphthalen-1-yl)-1,2,3-thiadiazol-5-ylthio)acetate

Procedure

NaOH (60% oil, 30 mg, 0.61 mmol) was added to a solution of 5-(1H-benzo[d][1,2,3]triazol-1-yl)-4-(naphthalen-1-yl)-1,2,3-thiadiazole and methylthioglycolate (64 mg, 0.61 mmol) in DMF (3 mL) and the mixture was stirred at room temperature for 2 h. 1N HCl was then added and the mixture was extracted with ethyl acetate, dried over Na2SO4 and concentrated. Purification by TLC (100% DCM) afforded methyl 2-(4-(naphthalen-1-yl)-1,2,3-thiadiazol-5-ylthio)acetate.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification by TLC (100% DCM)

Sources & evidence

ORD record
ord-468872f370f747c8a3bcc9b831102c70
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Reaction notes

Loading…