Hydrochloric Acid → N-(5-Bromonaphthalene-1-carbothioyl)-N-methylglycine

HRID 745780Notes

Reaction equation

HRID 745780 reaction equation
[OH-].[Na+].C[O:4][C:5](=[O:22])[CH2:6][N:7]([C:9]([C:11]1[C:20]2[C:15](=[C:16]([Br:21])[CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1)=[S:10])[CH3:8].Cl>CO>[Br:21][C:16]1[CH:17]=[CH:18][CH:19]=[C:20]2[C:15]=1[CH:14]=[CH:13][CH:12]=[C:11]2[C:9](=[S:10])[N:7]([CH3:8])[CH2:6][C:5]([OH:22])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 13318009HCID 13318009, compound

Product 1

HCID 13318010N-(5-Bromonaphthalene-1-carbothioyl)-N-methylglycineYield 75.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 1N aqueous NaOH solution (25 ml) was added to a suspension of N-[(5-bromo-1-napthalenyl)thioxomethyl]-N-methylglycine methyl ester (7.3 g, 20.7 mmoles; described in Example 3) in methanol (75 ml). The mixture was stirred at 20° to 22° C. for 21/2 hr, neutralized to pH 7 with aqueous HCl and concentrated under reduced pressure to remove methanol. The residual solution was rendered acidic (pH=2) with the addition of aqueous HCl solution and extracted with ethyl acetate. The extract was dried (MgSO4) and evaporated to dryness. The residue was crystallized from ethyl acetate-hexane to give 5.3 g of the title compound; mp 181° C.; NMR (DMSO-d6) δ 2.95 (s, 3H), 4.65 & 5.2 (2d, J=16.8, 2H), 7.85 (m, 6H), UVλmax (EtOH) 285 nm (ε12,300), 280 (12,400), 221 (42,600); IR(Nujol™) 2900, 1720 cm-1 ; Anal Calcd: C, 49.72% H, 3.58% N, 4.14%; Found: C, 49.63% H, 3.63% N, 4.18%.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customto remove methanol
  3. additionwith the addition of aqueous HCl solution
  4. extractionextracted with ethyl acetate
  5. dry with materialThe extract was dried (MgSO4)
  6. customevaporated to dryness
  7. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-1fac24f12e064c8db20d98877836822d
Source dataset
uspto-grants-1986_07
Patent number
US04600724

Reaction notes

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