Nitric Acid → HCID 14986507, compound

HRID 257217Notes

Reaction equation

HRID 257217 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][CH:9]2[CH:14]([OH:15])[C:13]([CH3:17])([CH3:16])[O:12][C:11]3[CH:18]=[CH:19][S:20][C:10]2=3)=[O:7])=[CH:4][CH:3]=1.[N+:23]([O-])([OH:25])=[O:24].[K+].[Br-]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:8][CH:9]2[CH:14]([OH:15])[C:13]([CH3:17])([CH3:16])[O:12][C:11]3[CH:18]=[C:19]([N+:23]([O-:25])=[O:24])[S:20][C:10]2=3)=[O:7])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 253877Potassium BromideHCID 149865067-(4-Chlorobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Product 1

HCID 14986507HCID 14986507, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared as described in Example 9 starting with 7-(4-chlorobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran (1.23 g, 3.64 mmol) and 90% nitric acid (1.5 mL) in acetic acid (20 mL) to give the product, 0.384 g (28%), as a yellow solid: mp 226°-229° C. dec; IR (KBr): 3315, 1655, 1535 and 1503 cm-1;MS: m/z 383 (MH+); 1H NMR (DMSO-d6): δ 1.25 (s, 3H), 1.44 (s, 3H), 3.90 (m, 1H, simplifies to d, J=8.9 Hz with D2O), 4.95 (m, 1H, simplifies to d, J=8.9 Hz, with D2O), 5.94 (d, J=6.0 Hz, 1H exchanges with D2O), 7.60 (d, J=8.6 Hz, 2H), 7.72 (s, 1H), 7.94 (d, J=8.6 Hz, 2H) and 9.11 (d, J=7.6 Hz, 1H, exchanges with D2O).

Workup

  1. customto give the product, 0.384 g (28%)

Sources & evidence

ORD record
ord-56a7be2c24d2450aa4ce43d4cb18f942
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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