Acetic Acid → 9-Methyl-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 50969Notes

Reaction equation

[CH3:1][C:2]1[C:12]2[S:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.CC(O)=O.[N:17]([O-])=[O:18].[Na+]>O>[CH3:1][C:2]1[C:12]2[S:11][CH2:10][CH2:9][CH2:8][N:7]([N:17]=[O:18])[C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of 9-methyl-2,3,4,5-tetrahydro-1,5-benzothiazepine (500 mg, 2.6 mmol) and AcOH (2 mL) cooled to ˜9° C. was added a solution of NaNO2 (212 mg, 3.1 mmol) and water (1 mL) dropwise over 4 min (internal temperature <12° C.). The cooling bath was removed and the reaction was maintained at 23° C. for 2 h. It was diluted with H2O (50 mL). 9-methyl-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine was obtained (470 mg, 87%) as a yellow solid after it was collected by vacuum filtration and air-dried at 23° C.

Workup

customThe cooling bath was removed
additionIt was diluted with H2O (50 mL)

Sources & evidence

ORD record: ord-2eef9b78ae0f46129dfc04595f2d0064
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06713471B1

Reaction notes

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