Sodium Hydroxide → HCID 178435041, compound

HRID 44333

Reaction equation

HRID 44333 reaction equation
[C:1]([C:3]1[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=1[NH:10][C:11]([NH:13]C(=O)C1C=CC=CC=1)=[S:12])#[N:2].[OH-].[Na+]>CCO>[NH2:2][C:1]1[C:3]2[C:7]([CH3:8])=[C:6]([CH3:9])[S:5][C:4]=2[NH:10][C:11](=[S:12])[N:13]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 899430N-benzoyl-N'-(3-cyano-4,5-dimethyl-2-thienyl)thiourea

Product 1

HCID 178435041HCID 178435041, compoundYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(3-cyano-4,5-dimethylthiophen-2-ylcarbamothioyl)benzamide (example 1a) (1.90 g, 6.03 mmol) and NaOH (2 N, 8.3 mL) in EtOH (25 mL) was stirred at 100° C. under nitrogen for half an hour. After cooling to room temperature, the clear reaction solution was filtered and the filtrate was carefully neutralized with 10% AcOH with vigorous stirring at 0° C. The resultant precipitate was collected by filtration, washed with warm water and then 20% EtOH in water to give the final product 4-amino-5,6-dimethylthieno[2,3-d]pyrimidine-2(1H)-thione (1.11 g, 87%) as an off-white solid. M.p.: >260° C. 1H NMR (400 MHz, DMSO-d6) δ2.25 (s, 3H), 2.26 (s, 3H). MS 212 (MH+).

Workup

  1. filtrationthe clear reaction solution was filtered
  2. filtrationThe resultant precipitate was collected by filtration
  3. washwashed with warm water

Sources & evidence

ORD record
ord-580783d52bf64d1c8c5dd8ecf4dc013e
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Linked notes

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