Dimethylformamide → 7-(4-Chlorobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

HRID 1086644Notes

Reaction equation

Br[CH:2]1[C:7]([CH3:9])([CH3:8])[O:6][C:5]2[CH:10]=[CH:11][S:12][C:4]=2[CH:3]1O.[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH2:21])=[O:20])=[CH:17][CH:16]=1.CN(C)C=[O:27]>>[Cl:14][C:15]1[CH:23]=[CH:22][C:18]([C:19]([NH:21][CH:3]2[CH:2]([OH:27])[C:7]([CH3:9])([CH3:8])[O:6][C:5]3[CH:10]=[CH:11][S:12][C:4]2=3)=[O:20])=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 120844-Chlorobenzamide

HCID 149864866-bromo-5,6-dihydro-7-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Product 1

HCID 149865067-(4-Chlorobenzamido)-5,6-dihydro-6-hydroxy-5,5-dimethyl-7H-thieno[3,2-b]pyran

Procedure

The title compound was prepared as described in Example 3 starting with 6-bromo-7-hydroxy-5,6-dihydro-5,5-dimethyl-7H-thieno[3,2-b]pyran (4.75 g, 18.1 mmol) and 4-chlorobenzamide (7.0 g, 45 mmol) in N,N-dimethylformamide (125 mL) to give 1.41 (23%) as a yellow solid: mp 196°-197° C.; IR (KBr): 3483, 3317, 1632 and 1525 cm-1 ; MS: m/z 338 (MH+); 1H NMR (DMSO-d6): δ1.20(s, 3H), 1.39(s, 3H), 3.79(m, 1H, simplifies to d, J=8.8 Hz, with D2O), 4.98(m, 1H, simplifies to d, J=8.8 Hz with D2O), 5.64(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), 7.56(d, J=6.8 Hz, 2H), 7.93(d, J=6.8 Hz, 2H) and 8.88(d, J=8.3 Hz, 1H, exchanges with D2O).

Sources & evidence

ORD record: ord-da29275f841c477fb85e60ee05b1e5b4
Source dataset: uspto-grants-1991_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05030736

Reaction notes

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