Water → HCID 57457071, compound

HRID 1361028Notes

Reaction equation

HRID 1361028 reaction equation
[N:1]1[NH:2][N:3]=[N:4][C:5]=1[C:6]1[CH:7]=[CH:8][C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=3.[C:19]1([C:25](Cl)([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C.O>CN(C)C=O>[C:19]1([C:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[N:3]2[N:2]=[N:1][C:5]([C:6]3[CH:7]=[CH:8][C:9]4[NH:10][C:11]5[C:16]([C:17]=4[CH:18]=3)=[CH:15][CH:14]=[CH:13][CH:12]=5)=[N:4]2)[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6456Trityl chlorideHCID 8471TriethylamineHCID 574570563-(1H-1,2,3,4-Tetrazol-5-yl)-9H-carbazole

Product 1

HCID 57457071HCID 57457071, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2H-Tetrazol-5-yl)-9H-carbazole (example 401, 17 g, 72.26 mmol) was dissolved in N,N-dimethylformamide (150 mL). Triphenylmethyl chloride (21.153 g, 75.88 mmol) and triethylamine (20.14 mL, 14.62 g, 144.50 mmol) were added consecutively. The reaction mixture was stirred for 18 hours at room temperature, poured into water (1.5 L) and stirred for an additional 1 hour. The crude product was filtered off and dissolved in dichloromethane (500 mL). The organic phase was washed with water (2×250 mL) and dried with magnesium sulfate (1 h). Filtration followed by concentration yielded a solid which was triturated in heptanes (200 mL). Filtration furnished 3-[2-(triphenylmethyl)-2H-tetrazol-5-yl]-9H-carbazole (31.5 g) which was used without further purification.

Workup

  1. stirringstirred for an additional 1 hour
  2. filtrationThe crude product was filtered off
  3. dissolutiondissolved in dichloromethane (500 mL)
  4. washThe organic phase was washed with water (2×250 mL)
  5. dry with materialdried with magnesium sulfate (1 h)
  6. filtrationFiltration
  7. concentrationfollowed by concentration
  8. customyielded a solid which
  9. customwas triturated in heptanes (200 mL)
  10. filtrationFiltration

Sources & evidence

ORD record
ord-d9a3a6479ca84f599a71954e3e4436d6
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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