Phosphorus oxychloride → HCID 136377377, compound

HRID 624160Notes

Reaction equation

HRID 624160 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][NH:9][C:10]([C:12]2[NH:13][CH:14]=[CH:15][CH:16]=2)=[O:11])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O>>[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[O:11][C:10]([C:12]3[NH:13][CH:14]=[CH:15][CH:16]=3)=[N:9][N:8]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 39967700HCID 39967700, compound

Product 1

HCID 136377377HCID 136377377, compound

Conditions

Temperature
120 °C

Procedure

To 1.2 g of N′-(4-bromobenzoyl)-1H-pyrrole-2-carbohydrazide (3.89 mmol) was added 5 ml phosphoryl trichloride (1.65 mmol). The reaction was stirred for 25 minutes at 120° C. The reaction was cooled to 0° C., and ice was added. The resulting solid was filtered, and washed with water, NH4OH, dichloromethane and ethyl acetate. Purification by silica gel chromatography (dichloromethane:methanol=9:1) resulted in the desired product. 1H NMR (400 MHz, DMSO-d6) δ 12.32 (s, 1H), 8.05-8.00 (m, 2H), 7.89-7.83 (m, 2H), 7.18 (td, J=1.5, 2.6, 1H), 6.97 (ddd, J=1.5, 2.4, 3.7, 1H), 6.33 (dt, J=2.4, 3.6, 1H). 13C NMR (400 MHz, DMSO-d6) δ 110.16, 112.49, 115.12, 122.71, 123.96, 125.23, 128.26, 132.49, 159.37, 161.57.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. additionice was added
  3. filtrationThe resulting solid was filtered
  4. washwashed with water, NH4OH, dichloromethane and ethyl acetate
  5. customPurification by silica gel chromatography (dichloromethane:methanol=9:1)

Sources & evidence

ORD record
ord-7122c55ff01b4781b1ce3002f9e60cd9
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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