Thionyl Chloride → HCID 44478661, compound

HRID 229369Notes

Reaction equation

HRID 229369 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)([C:13]2[NH:14][CH2:15][CH2:16][CH2:17][N:18]=2)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].O=S(Cl)[Cl:27]>C(Cl)(Cl)Cl>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([Cl:27])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[NH:14][CH2:15][CH2:16][CH2:17][N:18]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 44478386HCID 44478386, compound

Product 1

HCID 44478661HCID 44478661, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Under a nitrogen atmosphere, into a cold (0° C.) solution of (4-tert-butylphenyl)(phenyl)-1,4,5,6,-tetrahydropyrimidin-2-ylmethanol (2.7 g, 8.37 mmol) in CHCl3 was added SOCl2 (1.9 mL) over 10 minutes. The reaction mixture was heated at reflux temperature for 4 h and concentrated in vacuo. The resultant residue was dissolved in benzene and concentrated in vacuo to dryness twice. The final residue was crystallized from chloroform and ether to afford 2-[(4-tert-butyl-phenyl)(chloro)phenylmethyl]-1,4,5,6,-tetrahydropyrimidine as an off white solid (2.4 g, 84% yield, mp 79° C.). MS m/e (M+H)+ 341; 1H NMR (400 MHZ, DMSOd6) δ 1.26 (s, 9H), 1.90 (m, 2H) 3.43 (m, 4H), 7.26 (d, 2H), 7.35 (m, 2H), 7.48 (m, 5H), 9.42 (bs, 1H).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 4 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe resultant residue was dissolved in benzene
  5. concentrationconcentrated in vacuo to dryness twice
  6. customThe final residue was crystallized from chloroform and ether

Sources & evidence

ORD record
ord-e1d07feec9354959921d479040c06333
Source dataset
uspto-grants-2009_07
Patent number
US07563796B2

Reaction notes

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