Formic Acid → N-(4-Methylbenzoyl)phosphoramidic dichloride

HRID 2052128Notes

Reaction equation

HRID 2052128 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.[P:11]([Cl:16])(Cl)(Cl)(Cl)[Cl:12].Cl.C(O)=[O:19]>C(Cl)(Cl)(Cl)Cl>[Cl:12][P:11]([Cl:16])([NH:8][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=1)=[O:19]

Participants

6

Reactant 4

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 24819Phosphorus pentachlorideHCID 692744-Methylbenzamide

Product 1

HCID 14115791N-(4-Methylbenzoyl)phosphoramidic dichloride

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

A mixture of 53 g (0.39 mole) of 4-methylbenzamide, 81.7 g (0.39 mole) of phosphorus pentachloride and 500 ml of AR carbon tetrachloride was heated at 60°-70° until the HCl gas evolution had ceased. Solution was cooled to 30° where 18.6 g (0.39 mole) of 97% formic acid was added. Continued to stir for 30 min. following the addition, then filtered, washed with AR carbon tetrachloride and air-dried to give 74.5 g, m.p. 96.5°-98°.

Workup

  1. additionwas added
  2. additionthe addition
  3. filtrationfiltered
  4. washwashed with AR carbon tetrachloride
  5. customair-dried
  6. customto give 74.5 g, m.p. 96.5°-98°

Sources & evidence

ORD record
ord-5e357bac1a8a4e8bb0dce389bd4731f2
Source dataset
uspto-grants-1980_01
Patent number
US04182881

Reaction notes

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