Thionyl Chloride → HCID 46880047, compound

HRID 596922Notes

Reaction equation

HRID 596922 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:7]=[C:8]([NH:12][C:13](=[O:20])[O:14][CH2:15][C:16]#CCO)[CH:9]=[CH:10][CH:11]=1>C(Cl)CCl>[CH:10]1[CH:11]=[C:6]([Cl:5])[CH:7]=[C:8]([NH:12][C:13]([O:14][C:15]#[C:16][Cl:3])=[O:20])[CH:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 766204-Hydroxy-2-butynyl (3-chlorophenyl)carbamate

Product 1

HCID 46880047HCID 46880047, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

In another procedure on the same scale, the thionyl chloride in 25 ml of EDC was stirred at 65° while a warm solution of 4-hydroxy-2-butynyl N-(3-chlorophenyl)carbamate in 75 ml of EDC was added dropwise over a period of 60 minutes. After 17 hours at 65°, the solvent was evaporated to afford 6.5 g of barban which was analyzed by HPLC: barban -- 97.5% (w/w), biscarbamate -- 1.0% (w/w); bisurea -- 1.6% (w/w).

Workup

  1. additionwas added dropwise over a period of 60 minutes
  2. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e28b0ae59d974015bdacc10d44959efc
Source dataset
uspto-grants-1977_03
Patent number
US04012433

Reaction notes

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