Butyl nitrite → HCID 21101400, compound

HRID 1353076Notes

Reaction equation

HRID 1353076 reaction equation
[NH2:1][C:2]1[CH:26]=[CH:25][C:24]([O:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:23][C:3]=1[C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[C:9]([O:21][CH3:22])[CH:8]=1)=[O:5].[N:34](OCCCC)=O.C1CCN2C(=NCCC2)CC1>ClCCl.C(O)(C(F)(F)F)=O>[CH3:22][O:21][C:9]1[CH:8]=[C:7]([N:6]2[C:4](=[O:5])[C:3]3[CH:23]=[C:24]([O:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)[CH:25]=[CH:26][C:2]=3[N:1]=[N:34]2)[CH:12]=[CH:11][C:10]=1[O:13][CH2:14][CH2:15][N:16]1[CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 3

HCID 10996Butyl nitriteHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 21101398HCID 21101398, compound

Product 1

HCID 21101400HCID 21101400, compound

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of the free base of this amine (58 mg, 0.13 mmol) in dichloromethane (2 ml) was acidified with 5 drops of TFA then treated with butyl nitrite (100 ul). A deep orange colour formed immediately. After 1 minute, DBU was introduced dropwise until basic. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel (eluting with methanol-dichloromethane-aqueous ammonia) to give the title compound which crystallised as a pale yellow HCl salt on treatment with 1M HCl in ether;

Workup

  1. customA deep orange colour formed immediately
  2. customThe solvent was removed in vacuo
  3. customthe residue purified by flash chromatography on silica gel (eluting with methanol-dichloromethane-aqueous ammonia)

Sources & evidence

ORD record
ord-cd3206ccd33746c1a5216a370364830e
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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