Benzoyl chloride → HCID 14986534, compound

HRID 257225Notes

Reaction equation

HRID 257225 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[NH2:17][CH:18]1[CH:23]([OH:24])[C:22]([CH3:26])([CH3:25])[O:21][C:20]2[CH:27]=[CH:28][S:29][C:19]1=2>ClCCl>[C:1]([NH:17][CH:18]1[CH:23]([OH:24])[C:22]([CH3:25])([CH3:26])[O:21][C:20]2[CH:27]=[CH:28][S:29][C:19]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 14986532HCID 14986532, compound

Product 1

HCID 14986534HCID 14986534, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in Example 34 starting with benzoyl chloride (0.95 ml), triethylamine (3.3 ml, 23 mmol) and 7-amino-5,6-dihydro-6-hydroxY-5,5-dimethyl-7H-thieno[3,2-b]pyran (1.55 g, 7.78 mmol) in dichloromethane (35 ml) to give the product 1.07 g (45%) as a colorless solid; mp 219°-220° C.; IR(KBr):3398, 1657, 1526 and 1490 cm-1 ; MS:m/z 304 (MH+); 1H NMR (DMSO-d6):δ 1.21 (5,3H), 1.39 (5,3H), 3.81 (m,1H, simplifies to d, J=8.8 Hz, with D2O), 5.00 (m,1H simplifies to d, 5=8.8 Hz, with D2O), 5.61(d,J=6.0 Hz, 1H, exchanges with D2O), 6.58(d,J=5.3 Hz,1H), 7.29(d,J=5.3 Hz,1H), 7.47(m,3H), 7.92 (dd,J=1.3 Hz, J=8.2 Hz,2H) and 8.79 (d,J=8.3 Hz, 1H, exchanges with D2O).

Sources & evidence

ORD record
ord-3c3c1ed9e9514fc49d6368b8a5822854
Source dataset
uspto-grants-1993_11
Patent number
US05260453

Reaction notes

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