4-(Chloromethyl)-2-phenyl-1,3-thiazole → HCID 13503206, compound

HRID 256304Notes

Reaction equation

HRID 256304 reaction equation
[SH:1][C:2]1[N:12]2[C:13]3[C:8]([CH2:9][CH2:10][CH2:11]2)=[CH:7][CH:6]=[CH:5][C:4]=3[N:3]=1.Cl[CH2:15][C:16]1[N:17]=[C:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[S:19][CH:20]=1>C(O)C>[C:21]1([C:18]2[S:19][CH:20]=[C:16]([CH2:15][S:1][C:2]3[N:12]4[C:13]5[C:8]([CH2:9][CH2:10][CH2:11]4)=[CH:7][CH:6]=[CH:5][C:4]=5[N:3]=3)[N:17]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazoleHCID 178527763HCID 178527763, compound

Product 1

HCID 13503206HCID 13503206, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5,6-dihydro-2-mercapto[4H]imidazo [4,5,1-ij]quinoline (2.04 g, 10.7 mmol) in 1 N-sodium-hydroxide (10.7 ml) and ethanol (10 ml) was treated with 4-chloromethyl-2-phenylthiazole (2.25 g, 10.7 mmol) and the resulting solution heated under reflux for 5 mins. The mixture was concentrated in vacuo and the aqueous mixture extracted with ethyl acetate (2×50 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give a yellow oil which crystallised on trituration with diethyl ether (50 ml) to give the title compound (3.62 g, 93%), mp 116°-118° (Found: C, 66.4; H, 5.0; N, 11.3 C20H17N3S2 requires C, 66.1; H, 4.7; N, 11.6%).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureunder reflux for 5 mins
  3. concentrationThe mixture was concentrated in vacuo
  4. extractionthe aqueous mixture extracted with ethyl acetate (2×50 ml)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customto give a yellow oil which
  8. customcrystallised on trituration with diethyl ether (50 ml)

Sources & evidence

ORD record
ord-55cbdc06ba8448a89a8f0e839e292bef
Source dataset
uspto-grants-1987_10
Patent number
US04703044

Reaction notes

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