Diethyl Ether → HCID 13843747, compound

HRID 1719248Notes

Reaction equation

HRID 1719248 reaction equation
Cl[CH2:2][N:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.[Cl:17][C:18]1[CH:19]=[N:20][C:21](=[O:24])[NH:22][CH:23]=1.CCOCC>ClCCl>[CH2:9]([N:3]([CH2:2][N:22]1[CH:23]=[C:18]([Cl:17])[CH:19]=[N:20][C:21]1=[O:24])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 13843738HCID 13843738, compound

Product 1

HCID 13843747HCID 13843747, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-Chloromethyl-N-ethoxycarbonylbenzylamine (see German Offenlegungsschrift No. 2,119,518) (10 mmol) in dichloromethane (20 ml) was added dropwise with stirring to a solution of 5-chloropyrimidin-2-one hydrochloride (20 mmol) in dichloromethane (80 ml). The reaction mixture was stirred at room temperature for 2 hours, extracted with water, the solution dried (MgSO4) and evaporated. The residual crude product (yield 80%, 2.57 g) was triturated with ether to leave the title compound in 53% yield (1.70 g), m.p. 143° C. 1H NMR (CDCl3): δ1.31 and 4.22 (EtO), 4.73 (CH2Ph), 5.23 (CH2N), 7.20 (Ph), 8.03 and 8.38 (H-4, H-6, J 4 Hz). IR(KBr): 1670 cm-1 (CO), 1720 (CO-carbamate).

Workup

  1. extractionextracted with water
  2. dry with materialthe solution dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-f9b9997fd38a4e8c971b94a93ac7957f
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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