HCID 178523937, compound → HCID 178514162, compound

HRID 1715234Notes

Reaction equation

HRID 1715234 reaction equation
[NH:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]([NH:9]C(=O)C2C=CC=CC=2)=[S:8])=[N:2]1>[OH-].[Na+]>[NH:1]1[CH:5]=[CH:4][C:3]([NH:6][C:7]([NH2:9])=[S:8])=[N:2]1

Participants

3

Reactant 1

HCID 178523937HCID 178523937, compound

Product 1

HCID 178514162HCID 178514162, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of N-[(1H-pyrazol-3-ylamino)carbonothioyl]benzamide (22 g, 0.089 mol) in 10% NaOH solution (200 ml) is stirred at 80° C. for 45 min. The reaction mixture is cooled down to rt and the solvents are removed under vacuum. The residue is acidified with 2M HCl to pH=1 and then basified with ammonium hydroxide. The product is extracted with dichloromethane (4×100 ml). The combined extracts are dried and evaporated. The solid residue is purified by flash chromatography using chloroform/methanol (9/1) as eluent. N-1H-Pyrazol-3-ylthiourea is isolated as a solid (9 g; 75%). 1H NMR (DMSO-d6, 300 MHz): δ 5.88 (br s, 1H), 7.64 (s, 1H), 8.44 (br s, 1H), 9.02 (br s, 1H), 10.30 (br s, 1H), 12.47 (br s, 1H). HPLC (Method B), Rt: 3.88 min (purity: 99.4%). TLC: Chloroform/methanol (9/1): Rf−0.2. Mp: 130-132° C.

Workup

  1. customthe solvents are removed under vacuum
  2. extractionThe product is extracted with dichloromethane (4×100 ml)
  3. customThe combined extracts are dried
  4. customevaporated
  5. customThe solid residue is purified by flash chromatography

Sources & evidence

ORD record
ord-600dcb76dd56407c87453aa34da22f95
Source dataset
uspto-grants-2010_09
Patent number
US07799814B2

Reaction notes

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