4-Pivalamidopyridin-3-yl diethylcarbamodithioate → 4-Aminopyridin-3-yl diethylcarbamodithioate

HRID 2267316Notes

Reaction equation

HRID 2267316 reaction equation
[CH2:1]([N:3]([CH2:20][CH3:21])[C:4]([S:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH:13]C(=O)C(C)(C)C)=[S:5])[CH3:2]>CO.[OH-].[Na+]>[CH2:20]([N:3]([CH2:1][CH3:2])[C:4]([S:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[NH2:13])=[S:5])[CH3:21]

Participants

4

Reactant 1

HCID 146662254-Pivalamidopyridin-3-yl diethylcarbamodithioate

Product 1

HCID 146662264-Aminopyridin-3-yl diethylcarbamodithioateYield 62.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

An opaque solution of 4-pivalamidopyridin-3-yl diethylcarbamodithioate (21.9 g, 67 mmol) in methanol (220 mL) and 1 N sodium hydroxide (220 mL) was stirred at r.t. for 20 h. Tlc showed consumption of starting material. The clear yellow solution was diluted with water (500 mL). After letting the turbid solution stand for 5 min, crystals precipitated out. The solid was filtered off, washed with water (2×50 mL) and diethyl ether (3×50 mL), and air dried to afford 4-aminopyridin-3-yl diethylcarbamodithioate (10.05 g, 62%) as colorless plate like crystals. 1H NMR: δ (CDCl3, 400 MHz) 1.30 (t, J=7 Hz, 3 H), 1.44 (t, J=7 Hz, 3 H), 3.90 (q, J=7 Hz, 2 H), 4.03 (q, J=7 Hz, 2 H), 4.68 (br. s., 2 H), 6.65 (d, J=5.5 Hz, 1 H), 8.25-8.30 (m, 2 H).

Workup

  1. customconsumption of starting material
  2. additionThe clear yellow solution was diluted with water (500 mL)
  3. customfor 5 min
  4. customcrystals precipitated out
  5. filtrationThe solid was filtered off
  6. washwashed with water (2×50 mL) and diethyl ether (3×50 mL), and air
  7. customdried

Sources & evidence

ORD record
ord-92ab8fa10aef4556bdd35ff5806abc15
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

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