Acetone → HCID 178513892, compound

HRID 371121Notes

Reaction equation

HRID 371121 reaction equation
ClC=C[S:4]C(C(O)=O)C(OC)=O.[C:13]([Cl:18])(=O)[C:14](Cl)=O.C[N:20](C)[CH:21]=[O:22].[N-]=[N+]=[N-].[Na+].[CH3:28][C:29](C)=[O:30]>ClCCl.O>[C:21]([CH:28]([CH:14]=[CH:13][Cl:18])[C:29]([OH:30])=[S:4])(=[O:22])[NH2:20]

Participants

8

Reactant 5

HCID 180AcetoneHCID 6228DimethylformamideHCID 33557Sodium AzideHCID 65578Oxalyl chlorideHCID 53779291HCID 53779291, compound

Product 1

HCID 178513892HCID 178513892, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of methyl 2-(2-chlorovinyl)thio-2-carboxyacetate (1) (450 mg), oxalyl chloride (325 mg) and dimethylformamide (50 mg) is stirred in dichloromethane (2 ml) at room temperature for 30 minutes. To the mixture is added a solution of sodium azide (550 mg) dissolved in acetone (2 ml) and water (2 ml). The mixture is stirred for 30 minutes, diluted with dichloromethane, washed with water, and cencentrated in vacuo to give azide (2). Yield: 430 mg.

Workup

  1. washwashed with water

Sources & evidence

ORD record
ord-3cb2cd8b8de84b97ae26100577fca965
Source dataset
uspto-grants-1985_07
Patent number
US04529721

Reaction notes

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