Nitrogen → 3-(4-Isocyanatophenyl)-1,4-dihydroindeno[1,2-c]pyrazole

HRID 991016Notes

Reaction equation

HRID 991016 reaction equation
[NH:1]1[C:5]2[C:6]3[C:11]([CH2:12][C:4]=2[C:3]([C:13]2[CH:21]=[CH:20][C:16](C(O)=O)=[CH:15][CH:14]=2)=[N:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.CC[N:41]([CH2:44]C)CC.N#N>CN(C=O)C>[N:41]([C:16]1[CH:20]=[CH:21][C:13]([C:3]2[C:4]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[NH:1][N:2]=2)=[CH:14][CH:15]=1)=[C:44]=[O:29]

Participants

6

Reactant 4

HCID 947NitrogenHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 184158474-(1,4-Dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid

Product 1

HCID 184158263-(4-Isocyanatophenyl)-1,4-dihydroindeno[1,2-c]pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(1,4-dihydroindeno[1,2-c]pyrazol-3-yl)benzoic acid 1 (5.8 g, 20.99 mmol) in DMF (200 mL) were added diphenylphosphoryl azide (5.22 mL, 23.09 mmol) and Et3N (3.35 mL, 23.09 mmol). The reaction mixture was heated to about 80° C., for about 4 h, until no more N2 gas evolution was observed. The off-white precipitation was filtered off and washed with EtOAc (3×5 mL) and Et2O (3×5 mL). The solid was dried under vacuum to give quantitative yield of 2 that was used in the next step without further purification. Mp 338-339° C. IR (KBr) 2132, 1723,1582,1520

Workup

  1. customThe off-white precipitation
  2. filtrationwas filtered off
  3. washwashed with EtOAc (3×5 mL) and Et2O (3×5 mL)
  4. customThe solid was dried under vacuum

Sources & evidence

ORD record
ord-6a26c221dd204081a4f0b665b561d2b8
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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