Formic Acid → Phosphoramidic dichloride, (4-butoxybenzoyl)-

HRID 2052141Notes

Reaction equation

HRID 2052141 reaction equation
[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].[P:15]([Cl:20])(Cl)(Cl)(Cl)[Cl:16].C(O)=[O:22]>C(Cl)(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH:12][P:15]([Cl:20])([Cl:16])=[O:22])=[O:11])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 24819Phosphorus pentachlorideHCID 43063154-butoxybenzamide

Product 1

HCID 20378761Phosphoramidic dichloride, (4-butoxybenzoyl)-

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 76 g (0.39 mole) of 4-butoxybenzamide, 81.9 g (0.39 mole) of phosphorus pentachloride and 700 ml of AR carbon tetrachloride was heated at 70° for 30 min. The resulting solution was cooled to 30° and 18.7 g (0.39 mole) of 97% formic acid was added. The reaction was chilled to 0°, filtered, washed with AR carbon tetrachloride and air-dried to give 52.1 g, m.p. 97°-98°.

Workup

  1. temperaturewas heated at 70° for 30 min
  2. temperatureThe resulting solution was cooled to 30°
  3. temperatureThe reaction was chilled to 0°
  4. filtrationfiltered
  5. washwashed with AR carbon tetrachloride
  6. customair-dried
  7. customto give 52.1 g, m.p. 97°-98°

Sources & evidence

ORD record
ord-67b734de37604d66875341da34177a27
Source dataset
uspto-grants-1980_01
Patent number
US04182881

Reaction notes

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