Water → 7-Fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine

HRID 1789950Notes

Reaction equation

HRID 1789950 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:12]=1.[N:13]([O-])=[O:14].[Na+].O>C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][N:7]([N:13]=[O:14])[C:6]=2[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22036736HCID 22036736, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 220367967-Fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepineYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

7-fluoro-2,3,4,5-tetrahydro-1,5-benzothiazepine (423 mg, 2.3 mmol) was dissolved in acetic acid (1.15 mL) at 0° C. in an ice bath. 2.7 M aqueous sodium nitrite (1 mL) was added and this was stirred over night. Water was added (100 mL) and extracted with dichloromethane (3×50 mL), the organics were combined and concentrated to give 7-fluoro-5-nitroso-2,3,4,5-tetrahydro-1,5-benzothiazepine (449 mg, 92%). 1H NMR (CDCl3, 300 MHz): δ 7.43 (t, 1H, J=7.1 Hz), 7.30 (dd, 1H, J=9.1 Hz, J=9.2 MHz), 7.26–7.00 (m, 1H), 4.18 (t, 2H, J=5.8 Hz), 2.86 (t, 2H, J=7.2 Hz), 2.17–2.04 (m, 2H) ppm.

Workup

  1. extractionextracted with dichloromethane (3×50 mL)
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-2b1821aff72a4f1a911f040b4d3ed9ed
Source dataset
uspto-grants-2006_07
Patent number
US07071186B2

Reaction notes

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