Dimethylformamide → HCID 46880047, compound

HRID 596921Notes

Reaction equation

HRID 596921 reaction equation
S(Cl)([Cl:3])=O.CN(C)C=O.[Cl:10][C:11]1[CH:12]=[C:13]([NH:17][C:18](=[O:25])[O:19][CH2:20][C:21]#CCO)[CH:14]=[CH:15][CH:16]=1>C(Cl)CCl>[CH:15]1[CH:16]=[C:11]([Cl:10])[CH:12]=[C:13]([NH:17][C:18]([O:19][C:20]#[C:21][Cl:3])=[O:25])[CH:14]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 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 preparation on the same scale, the thionyl chloride and dimethylformamide in 25 ml of EDC were 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 60 minutes. Barban (6.5 g) was obtained by evaporation of the solvent after 17 hours at 65° and analyzed by HPLC: barban 97.6% (w/w); biscarbanate -- 2.2% (w/w); bisurea -- 1.6% (w/w).

Workup

  1. customIn another preparation on the same scale
  2. additionwas added dropwise over 60 minutes

Sources & evidence

ORD record
ord-98c0e9df43684f7cb0ffb5a6103c34c4
Source dataset
uspto-grants-1977_03
Patent number
US04012433

Reaction notes

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