Triethylamine → 2-(5-Nitro-2-thienyl)thio-5-chloropyrimidine

HRID 905224Notes

Reaction equation

HRID 905224 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.Br[C:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=1.[OH-].[Na+]>ClCCl.O>[N+:22]([C:19]1[S:18][C:17]([S:8][C:5]2[N:6]=[CH:7][C:2]([Cl:1])=[CH:3][N:4]=2)=[CH:21][CH:20]=1)([O-:24])=[O:23]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 832222-Bromo-5-nitrothiopheneHCID 71403455-Chloro-2(1H)-pyrimidinethione

Product 1

HCID 204757562-(5-Nitro-2-thienyl)thio-5-chloropyrimidineYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 5-chloropyrimidine-2-thione (7.5 mmol), triethylamine (9 mmol) and 2-bromo-5-nitrothiophene (9 mmol) in dichloromethane (50 ml) was stirred at room temperature for 2 days. The resultant solution was then diluted with dichloromethane (50 ml), the solution shaken with 1 M NaOH (2×10 ml) and subsequently with water (10 ml), the dried (MgSO4) solution evaporated and the solid residue recrystallized from pet. ether; yield 63%, m.p. 141°-143° C. 1H NMR (CDCl3): δ7.16 and 7.83 (H-31, H-41), 8.53 (H-4, H-6).

Workup

  1. dry with materialthe dried (MgSO4) solution
  2. customevaporated
  3. customthe solid residue recrystallized from pet. ether

Sources & evidence

ORD record
ord-d0829dbe87934c4d80635ad336640ca3
Source dataset
uspto-grants-1983_12
Patent number
US04423047

Reaction notes

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