Dichloromethane → 1,2,3,5,6,7-Hexahydro-4-isocyanato-s-indacene

HRID 990601Notes

Reaction equation

[CH2:1]1[C:12]2[C:4](=[C:5]([NH2:13])[C:6]3[CH2:7][CH2:8][CH2:9][C:10]=3[CH:11]=2)[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:21](Cl)(Cl)=[O:22].C(Cl)Cl>O1CCCC1.C1(C)C=CC=CC=1>[N:13]([C:5]1[C:4]2[CH2:3][CH2:2][CH2:1][C:12]=2[CH:11]=[C:10]2[C:6]=1[CH2:7][CH2:8][CH2:9]2)=[C:21]=[O:22]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 1.77 g (0.01 mole) of 1,2,3,5,6,7-hexahydro-s-indacen-4-ylamine IX (Vejdelek et al. Coll. Czech Chem. Comm. 42: 3094 (1977) and 1.11 g (0.011 mole) of triethylamine in 25 mL of tetrahydrofuran was added 5.7 mL (0.011 mole) of a 1.93 M solution of phosgene in toluene. The reaction was stirred at room temperature for 15 min and at 70° C. for 15 min. The solvents were evaporated in vacuo. The residue was dissolved in hexane and purified on a plug of silica gel eluting with 10% CH2Cl2/hexane to give 1.79 g of non-labeled X (90%); mp 40-41° C. TLC:Hex/CH2Cl2::2/1 single-spot material Rƒ 0.70.1H-NMR (300 MHz CDCl3) δ: (2.13, t, 4H), (2.85, m, 8H), (6.93, s, 1H).

Workup

customThe solvents were evaporated in vacuo
dissolutionThe residue was dissolved in hexane
custompurified on a plug of silica gel eluting with 10% CH2Cl2/hexane
customto give 1.79 g of non-labeled X (90%)

Sources & evidence

ORD record: ord-b28aa1c465c04956bc1a37b4cff30bd6
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06461822B2

Reaction notes

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