Toluene → HCID 12893610, compound

HRID 1112306Notes

Reaction equation

HRID 1112306 reaction equation
[CH2:1]1[C:6]2[S:7][C:8]3[N:12]([C:5]=2[CH2:4][CH2:3][NH:2]1)[C:11]1[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=1[N:9]=3.[C:17]1([CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C.C(Br)C1C=CC=CC=1>C(OCC)(=O)C>[C:17]1([CH2:23][N:2]2[CH2:3][CH2:4][C:5]3[N:12]4[C:11]5[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=5[N:9]=[C:8]4[S:7][C:6]=3[CH2:1]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1140Toluene2×HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 12893604HCID 12893604, compound

Product 1

HCID 12893610HCID 12893610, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1,2,3,4-tetrahydropyrido[4',3':4,5]thiazolo[3,2-a]benzimidazole (1.9 g., 0.008 mole) is dissolved in 100 ml. of boiling toluene. Triethylamine (5 ml.) is added at 80°. Benzyl bromide (1.7 g., 0.01 mole) is dissolved in 5 ml. of toluene and added dropwise to the reaction mixture. After the addition, the reaction mixture is refluxed for two hours. It is filtered and concentrated in vacuo to yield 3.6 g. of oil. Ethyl acetate is added and the product, 1,2,3,4-tetrahydro-2-(phenylmethyl)pyrido[4',3':4,5]thiazolo[3,2-a]benzimidazole crystallizes. This is filtered and recrystallized from ethyl acetate:ethanol (10:1) to yield 1.4 g. of analytical product, m.p. 124°-129°.

Workup

  1. additionAfter the addition
  2. temperaturethe reaction mixture is refluxed for two hours
  3. filtrationIt is filtered
  4. concentrationconcentrated in vacuo
  5. customto yield 3.6 g
  6. customthe product, 1,2,3,4-tetrahydro-2-(phenylmethyl)pyrido[4',3':4,5]thiazolo[3,2-a]benzimidazole crystallizes
  7. filtrationThis is filtered
  8. customrecrystallized from ethyl acetate:ethanol (10:1)
  9. customto yield 1.4 g

Sources & evidence

ORD record
ord-1744348d363e43e8af77134c187e9444
Source dataset
uspto-grants-1978_10
Patent number
US04122083

Reaction notes

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