Propargyl bromide → HCID 12958928, compound

HRID 905216Notes

Reaction equation

HRID 905216 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5](=[S:8])[NH:6][CH:7]=1.C(N(CC)CC)C.[CH2:16](Br)[C:17]#[CH:18]>ClCCl>[CH2:18]([S:8][C:5]1[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=1)[C:17]#[CH:16]

Participants

5

Reactant 3

HCID 7842Propargyl bromideHCID 8471TriethylamineHCID 71403455-Chloro-2(1H)-pyrimidinethione

Product 1

HCID 12958928HCID 12958928, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloropyrimidine-2-thione (5 mmol) and triethylamine (5 mmol) was stirred together in dichloromethane (40 ml) for 5 min before propargyl bromide (6 mmol) was added. The mixture was stirred at room temperature for 1 h before the solvent was evaporated. The residue was triturated with water (20 ml), and the solid recrystallized from methanol; yield 87%, m.p. 66° C. 1H NMR (CDCl3): δ2.16 (HC≡, t, J 2 Hz), 3.88 (CH2, d, J 2 Hz), 8.80 (H-4, H-6). IR (KBr): 3300 Cm-1 (HC≡).

Workup

  1. additionwas added
  2. customwas evaporated
  3. customThe residue was triturated with water (20 ml)
  4. customthe solid recrystallized from methanol

Sources & evidence

ORD record
ord-e981ae306b684c6ca225e369280d7c97
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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