Nitric Acid → HCID 18948914, compound

HRID 981501Notes

Reaction equation

HRID 981501 reaction equation
[OH:1][CH:2]1[CH2:7][O:6][C:5]2[CH:8]=[CH:9][S:10][C:4]=2[CH:3]1[NH:11][C:12](=[O:23])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1.[N+:24]([O-])([OH:26])=[O:25].[K+].[Br-]>C(O)(=O)C>[OH:1][CH:2]1[CH2:7][O:6][C:5]2[CH:8]=[C:9]([N+:24]([O-:26])=[O:25])[S:10][C:4]=2[CH:3]1[NH:11][C:12](=[O:23])[C:13]1[CH:14]=[CH:15][C:16]([C:19]([F:22])([F:20])[F:21])=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 253877Potassium BromideHCID 18948924HCID 18948924, compound

Product 1

HCID 18948914HCID 18948914, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared as described in Example 9 starting with 5,6-dihydro-6-hydroxy-7-(4-trifluoromethylbenzamido)-7H-thieno[3,2-b]pyran (1.5 g, 4.04 mmol) and 90% nitric acid (2.5 mL) in acetic acid (20 mL) to give a yellow solid, 0.165 g (10%): mp 219°-220° C.; IR (KBr): 3310, 1661, 1538 and 1504 cm-1 ; MS: m/z 417 (MH+); 1H NMR (DMSO-d6): δ 1.26 (s, 3H), 1.45 (s, 3H), 3.92 (m, 1H, simplifies to d, J=8.9 Hz, with D2O), 4.98 (m, 1H, simplifies to d, J=8.9 Hz, with D2O), 5.99 (d, 1H, exchanges with D2O), 7.74 (s, 1H), 7.92 (d, J=8.5 Hz, 2H), 8.12 (d, J=8.5 Hz, 2H) and 9.30 (d, 1H, exchanges with D2O).

Workup

  1. customto give a yellow solid, 0.165 g (10%)

Sources & evidence

ORD record
ord-126aad9b20824344a9087e92f0ea8134
Source dataset
uspto-grants-1991_02
Patent number
US04992435

Reaction notes

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