Acetic Acid → HCID 22036759, compound

HRID 1267034Notes

Reaction equation

HRID 1267034 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][C:7](=[O:11])[C:6]=2[CH:12]=1.C(O)(=O)C.[N-:17]=[N+]=[N-].[Na+].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:10][CH2:9][CH2:8][C:7](=[O:11])[NH:17][C:6]=2[CH:12]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 27375216-Fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one

Product 1

HCID 22036759HCID 22036759, compoundYield 75.1%

Conditions

Temperature
50 °C

Procedure

6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one (100 mg, 0.54 mmol ) was dissolved in acetic acid (0.5 mL, 1.1 eq), sodium azide (71.2 mg, 1.1 mmol) was added and mixture was heated to 50° C. Sulfuric acid (0.13 mL, 4.3 eq) was added slowly and stirred at 50° C. for 1.5 hours. Ice chips (150 mg) were added and a green solid precipitated, this was filtered, washed with water and dried to give 7-fluoro-2,3-dihydro-1,5-benzothiazepin-4(5H)-one (80 mg, 24%). 1H NMR (CDCl3, 300 MHz): δ 7.77 (s-broad, 1H), 7.69 (t, 1H, J=7.3 Hz), 6.94-6.82 (m, 2H), 3.42 (t, 2H, J=7 Hz), 2.63 (t, 2H, J=6.7 Hz) ppm.

Workup

  1. additionIce chips (150 mg) were added
  2. customa green solid precipitated
  3. filtrationthis was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d091ab676a2e429590e7cba511d46352
Source dataset
uspto-grants-2003_04
Patent number
US06552017B1

Reaction notes

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