Dimethylformamide → HCID 18958827, compound

HRID 1708423Notes

Reaction equation

HRID 1708423 reaction equation
[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6](O)[C:5]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=2)=[CH:15][CH:14]=1)[CH2:2][CH3:3].CN(C)C=O.S(Cl)([Cl:39])=O>>[CH2:1]([C:4]1[N:9]=[C:8]([CH3:10])[N:7]=[C:6]([Cl:39])[C:5]=1[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=2)=[CH:15][CH:14]=1)[CH2:2][CH3:3]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 178440129HCID 178440129, compound

Product 1

HCID 18958827HCID 18958827, compound

Procedure

1.5 g of 6-n-propyl-2-methyl-4-hydroxy-5-{[2'-(4,4-dimethyl-2-oxazolinyl)-4-biphenylyl]methyl}pyrimidine, prepared in Example 184, are dissolved in 3 ml of thionyl chloride. 0.1 ml of dimethylformamide is added and the mixture is stirred for 1 hour at room temperature. The thionyl chloride is evaporated off under vacuum without heating, and the residue is washed with ether, then alkalinised with ammonium hydroxide solution and washed with water. The ether phase is evaporated under vacuum to give 0.6 g of 6-n-propyl-2-methyl-4-chloro-5-{[2'-(4,4-dimethyl-2-oxazolinyl)-4-biphenylyl]methyl}pyrimidine in the form of an oil, which is used without further purification for the next step.

Workup

  1. customThe thionyl chloride is evaporated off under vacuum
  2. temperaturewithout heating
  3. washthe residue is washed with ether
  4. washwashed with water
  5. customThe ether phase is evaporated under vacuum

Sources & evidence

ORD record
ord-7e5c6dcf230745e7b9ea7f6ace8fc454
Source dataset
uspto-grants-1994_10
Patent number
US05358950

Reaction notes

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