Hydrochloric Acid → HCID 85439451, compound

HRID 2389548Notes

Reaction equation

HRID 2389548 reaction equation
Cl.[S:2]([N:12]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[C:14]2[CH:20]=[CH:21][CH:22]=[CH:23][C:13]1=2)([C:5]1[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[N:24](OCCC(C)C)=[O:25]>C(OCC)C>[OH:25][N:24]=[C:16]1[CH2:17][CH2:18][N:12]([S:2]([C:5]2[CH:11]=[CH:10][C:8]([CH3:9])=[CH:7][CH:6]=2)(=[O:3])=[O:4])[C:13]2[CH:23]=[CH:22][CH:21]=[CH:20][C:14]=2[C:15]1=[O:19]

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 8053Isoamyl NitriteHCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

Product 1

HCID 85439451HCID 85439451, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Hydrochloric acid gas was bubbled through a cooled suspension of 1-tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one (30 g, 0.1 mol) in a dry diethyl ether (500 mL) at 0-5° C. Isoamyl nitrite (26.41 mL, 0.24 mol) was added drop wise and hydrochloric acid gas was continuously passed for 6-7 h after the addition. The precipitate that formed was filtered washed with diethyl ether and dried under reduced pressure to afford 4-(hydroxyimino)-1-tosyl-3,4-dihydro-1H-benzo[b]azepin-5 (2H)-one (21.09 g). 1H NMR: 400 MHz, CDCl3) δ: 7.79 (1H, d, J=7.6 Hz), 7.2 (1H, t, J=7.6 Hz), 7.62 (1H, d, J=8.0 Hz), 7.55 (1H, t, J=7.2 Hz), 7.39 (2H, d, J=8.4 Hz), 7.16 (2H, d, J=8.4 Hz), 4.07 (2H, t, J=6.8 Hz), 2.88 (2H, t, J=6.8 Hz), 2.342 (3H, s), 1.98 (2H, m).

Workup

  1. additionafter the addition
  2. customThe precipitate that formed
  3. filtrationwas filtered
  4. washwashed with diethyl ether
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-9521ba0b87794ba69ffecd585f2e2995
Source dataset
uspto-grants-2012_09
Patent number
US08273754B2

Reaction notes

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