1,2-Dichloroethane → HCID 66599382, compound

HRID 1889045Notes

Reaction equation

HRID 1889045 reaction equation
[CH3:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[N:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[NH:24]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[NH2:25]>ClCCl>[CH3:1][C:2]1[S:6][C:5]([C:7]([NH:25][NH:24][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:9])=[N:4][CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 218773495-Methyl-1,3-thiazole-2-carboxylic acid

Product 1

HCID 66599382HCID 66599382, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 5-methyl-1,3-thiazole-2-carboxylic acid (500 mg, 3.49 mmol) in dry dichloromethane (DCM) (17.500 ml) was stirred at room temperature under an atmosphere of argon. EDC (803 mg, 4.19 mmol) and HOBT (267 mg, 1.746 mmol) were added to the stirred solution. After 15 minutes, 1,1-dimethylethyl hydrazinecarboxylate (554 mg, 4.19 mmol) was added to the stirred solution. The resulting solution was stirred for 18 hours. After this time, the solution was diluted with DCM (approx. 50 ml) and washed with water (2× approx. 20 ml). The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow coloured oil of desired product in 451 mg.

Workup

  1. washwashed with water (2× approx. 20 ml)
  2. dry with materialThe organic extracts were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0fef6f43270a4c48a1e62ee19d87febc
Source dataset
uspto-grants-2013_08
Patent number
US08501946B2

Reaction notes

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