N,N-Dimethylaniline → HCID 178478405, compound

HRID 1883555Notes

Reaction equation

HRID 1883555 reaction equation
CN(C)C1C=CC=CC=1.P(Cl)(Cl)([Cl:12])=O.[N:15]1([CH2:21][CH2:22][NH:23][C:24]2[NH:25][C:26](=O)[C:27]3[N:28]=[CH:29][NH:30][C:31]=3[N:32]=2)[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1>>[Cl:12][C:26]1[N:25]=[C:24]([NH:23][CH2:22][CH2:21][N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[N:32]=[C:31]2[C:27]=1[N:28]=[CH:29][NH:30]2

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychloride2×HCID 178518718HCID 178518718, compound

Product 1

HCID 178478405HCID 178478405, compoundYield 88.7%

Procedure

A mixture of N,N-dimethylaniline (4 ml, 31 mmol) and phosphorus oxychloride (30 ml, 314 mmol) was stirred at ambient temperature for 10 min before Intermediate 37 (5.5 g, 20 mmol) was added portionwise and was then refluxed for 15 min. On cooling the phosphorus oxychloride was evaporated in vacuo, the residue obtained was azeotroped with toluene (3×50 ml). Purification using flash column chromatography with a Biotage column (90 g, SiO2) eluting with 10% methanol/chloroform 1% ammonia gave the title compound as a pale yellow solid (4.980 g). LC/MS SYSTEM C Rt=1.61 min, m/z=281 MH+.

Workup

  1. additionwas added portionwise
  2. temperaturewas then refluxed for 15 min
  3. customwas evaporated in vacuo
  4. customthe residue obtained
  5. customwas azeotroped with toluene (3×50 ml)
  6. customPurification
  7. washeluting with 10% methanol/chloroform 1% ammonia

Sources & evidence

ORD record
ord-a2e9e521236c4510ae3a26ff0bcaf60a
Source dataset
uspto-grants-2004_07
Patent number
US06762170B1

Reaction notes

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