Triethylamine → HCID 12477074, compound

HRID 1723355Notes

Reaction equation

HRID 1723355 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[S:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C(OC(Cl)=O)C(C)C.O.[NH2:27][NH2:28]>C1COCC1.CCOCC>[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:27][NH2:28])=[S:7])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 62365Isobutyl chloroformateHCID 1784259114-Methylthiobenzoic acid

Product 1

HCID 12477074HCID 12477074, compoundYield 27.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To p-methylthiobenzoic acid (1.68 g, 10 mmol) in THF (20 ml) were added triethylamine (1.39 ml, 10 mmol) and isobutylchloroformate (1.31 ml, 10 m). After 20 min at 20° C. ether (20 ml) was added, the mixture filtered, and hydrazine hydrate (0.49 ml, 10 mmol) added to the filtrate. After 1 h at 20° C. the solution was evaporated in vacuo and the residue recrystallised from water to give p-methylthiobenzohydrazide as short colourless needles (0.45 g, 25%); m.p. 140°-142° C.; δH (dmso-d6) 9.6 (1H, bs, NH), 7.2, 7.7 (4H, ABq, aryl), 3.8 (2H, bs, NH2), 2.5 (3H, s, sMe).

Workup

  1. filtrationthe mixture filtered
  2. customAfter 1 h at 20° C. the solution was evaporated in vacuo
  3. customthe residue recrystallised from water

Sources & evidence

ORD record
ord-9bdf7b6afeb847499260e7e6935148e5
Source dataset
uspto-grants-1989_08
Patent number
US04861788

Reaction notes

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