Dimethylformamide → HCID 88508586, compound

HRID 654528Notes

Reaction equation

HRID 654528 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[C:11]([CH:13]([O:15][C:16]([C:18]1[NH:19][CH:20]=[C:21]([CH2:25][CH3:26])[C:22]=1[CH2:23][CH3:24])=[O:17])[CH3:14])#[N:12].C([O-])(=O)C.[Na+]>ClC(Cl)C>[C:11]([CH:13]([O:15][C:16]([C:18]1[NH:19][C:20]([CH:8]=[O:9])=[C:21]([CH2:25][CH3:26])[C:22]=1[CH2:23][CH3:24])=[O:17])[CH3:14])#[N:12]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24813Phosphorus oxychlorideHCID 517045Sodium AcetateHCID 131717468HCID 131717468, compound

Product 1

HCID 88508586HCID 88508586, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent2×

Procedure

15 ml (160 mmol) phosphorous oxychloride were added dropwise for a period of 20 minutes to 13 ml (160 mmol) dimethylformamide at a temperature of 0° C. The mixture was stirred for another 15 minutes at room temperature and then 100 ml of dichloroethane were added. A solution of 10 g (40 mmol) of compound 11 in 50 ml dichloroethane were added dropwise. After gentle reflux for 15 minutes, the mixture was poured into 500 ml of a 4-molar sodium acetate solution and heated for a further 15 minutes. The organic layer was separated, washed with water and yielded after evaporation of the solvent, a brown oil, which was directly used for the next step without purification.

Workup

  1. temperatureAfter gentle reflux for 15 minutes
  2. temperatureheated for a further 15 minutes
  3. customThe organic layer was separated
  4. washwashed with water
  5. customyielded
  6. customafter evaporation of the solvent
  7. customa brown oil, which was directly used for the next step without purification

Sources & evidence

ORD record
ord-ee067b2aee734d28b451632ec3c23ca3
Source dataset
uspto-grants-1992_07
Patent number
US05132101

Reaction notes

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