Triethylamine → HCID 53845013, compound

HRID 358559Notes

Reaction equation

HRID 358559 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:10]=[C:11]=[S:12])[CH:8]=2)[CH:3]=[N:2]1.Cl.[CH2:14]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH2:20])[CH3:15].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:14]([O:16][C:17](=[O:21])[CH2:18][CH2:19][NH:20][C:11](=[S:12])[NH:10][C:7]1[CH:8]=[C:9]2[C:4]([CH:3]=[N:2][NH:1]2)=[CH:5][CH:6]=1)[CH3:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 458475beta-Alanine, ethyl ester, hydrochlorideHCID 21611747HCID 21611747, compound

Product 1

HCID 53845013HCID 53845013, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 5 g (28.6 mmol) of lH-indazol-6-yl isothiocyanate, 5.3 g (34.3 mmol) of beta-alanine ethyl ester hydrochloride and 4.8 ml (34.3 mmol) of triethylamine in 50 ml of chloroform is left at room temperature under agitation for one hour. The chloroform phase is washed with water (2 × 10 ml) and with a 1 N hydrochloric acid solution (2 × 10 ml). It is dried and concentrated to dryness. The residue (8 g) is triturated in ethyl ether (3 × 20 ml). There is obtained 3.1 g of (lH-indazol-6-yl)thiocarbamoyl-beta-alanine ethyl ester (yield 28%, melting point 145° C.).

Workup

  1. washThe chloroform phase is washed with water (2 × 10 ml) and with a 1 N hydrochloric acid solution (2 × 10 ml)
  2. customIt is dried
  3. concentrationconcentrated to dryness
  4. customThe residue (8 g) is triturated in ethyl ether (3 × 20 ml)

Sources & evidence

ORD record
ord-d519790db44e4d6fbdb58849fe1a11da
Source dataset
uspto-grants-1991_03
Patent number
US04997667

Reaction notes

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