Chloroform → 1-[(Benzylsulfanyl)(phenyl)methyl]-5-chloropyrimidin-2(1H)-one

HRID 1719249Notes

Reaction equation

HRID 1719249 reaction equation
[CH2:1]([S:8][CH:9](Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[Cl:18][C:19]1[CH:20]=[N:21][C:22](=[O:25])[NH:23][CH:24]=1.C(N(CC)CC)C.C(Cl)(Cl)Cl>C(Cl)Cl>[CH2:1]([S:8][CH:9]([N:23]1[CH:24]=[C:19]([Cl:18])[CH:20]=[N:21][C:22]1=[O:25])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 12296042Benzene, [chloro[(phenylmethyl)thio]methyl]-HCID 126485235-Chloropyrimidin-2-ol hydrochloride

Product 1

HCID 138437511-[(Benzylsulfanyl)(phenyl)methyl]-5-chloropyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

α-Chlorobenzyl benzyl sulphide (see R. H. Mitchell, Tetrahedron Letters 44, 4395 (1973) (4 mmol) in CH2Cl2 (10 ml) was added dropwise over a period of 5 minutes at 0° C. to a mixture of 5-chloropyrimidin-2-one hydrochloride (4 mmol) and triethylamine (8 mmol) in CH2Cl2 (30 ml). The mixture was stirred for 3 hours at room temperature and 1/2 hour at 40° C. before chloroform (20 ml) was added and the solution washed with water (3 times). The dried (MgSO4) solution was evaporated, ether added to the crude product and the insoluble product collected. Yield 0.35 g (26%), m.p. 118° C. 1H-NMR (CDCl3): δ(CH2) 7.12 (--CH--), 7.27 (Ph), 7.33 (Ph), 8.12 (H-4, d, J 3 Hz)), 8.30 (H-6, d, J 3 Hz).

Workup

  1. additionwas added
  2. washthe solution washed with water (3 times)
  3. dry with materialThe dried (MgSO4) solution
  4. customwas evaporated
  5. additionether added to the crude product
  6. customthe insoluble product collected

Sources & evidence

ORD record
ord-ab1818cc0ff94f78b835f7c7a6464624
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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