Dimethylformamide → HCID 13526425, compound

HRID 444290Notes

Reaction equation

HRID 444290 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([SH:26])[NH:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Cl[CH2:28][CH2:29]Br.CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]3[C:13]([S:26][CH2:28][CH2:29]3)=[N:14][C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=2)=[CH:9][CH:10]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178474105HCID 178474105, compound

Product 1

HCID 13526425HCID 13526425, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 10.0 g. (0.027 mole) of 4,5-bis-(p-acetamidophenyl)-2-mercaptoimidazole and 4.9 g. (0.034 mole) of 2-chloroethyl bromide in 80 ml. of sieve dried dimethylformamide was refluxed with stirring under nitrogen for 75 minutes. Potassium carbonate (3.8 g., 0.027 mole) was added and the suspension was refluxed for 2 hours, then allowed to cool to room temperature and poured into 650 ml. of water. The gum which formed was filtered off and crystallized from 50 ml. of hot methanol. The crystals were washed with cold methanol and ether and air dried to give 5,6-bis(p-acetamidophenyl)-2,3-dihydroimidazo[2,1-b]thiazole, m.p. 285°-290° C.

Workup

  1. additionA mixture of 10.0 g
  2. temperaturethe suspension was refluxed for 2 hours
  3. additionpoured into 650 ml
  4. customThe gum which formed
  5. filtrationwas filtered off
  6. customcrystallized from 50 ml
  7. washThe crystals were washed with cold methanol and ether and air
  8. customdried

Sources & evidence

ORD record
ord-e57405c2047f4ab3ad461e52a34bc4cf
Source dataset
uspto-grants-1981_04
Patent number
US04263311

Reaction notes

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