Formaldehyde → 1-(7-Methoxy-2,3-dihydro-1,4-benzothiazepin-4(5H)-yl)prop-2-en-1-one

HRID 1917082Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9][CH2:10][CH2:11][NH:12][C:13](=[O:16])[CH:14]=[CH2:15])=[CH:5][CH:4]=1.C=O.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]2[S:9][CH2:10][CH2:11][N:12]([C:13](=[O:16])[CH:14]=[CH2:15])[CH2:19][C:5]=2[CH:4]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of compound 32 (280 mg), paraformaldehyde (600 mg), p-toluenesulfonic acid (140 mg) in benzene (7.0 mL) was stirred at 80° C. for 16 h. The reaction mixture was filtered and washed with sat. NaHCO3 solution (2×3 mL). The solvents were removed by evaporation under reduced pressure to give product 33 as an oil. Yield: 253 mg, 86%.

Workup

filtrationThe reaction mixture was filtered
washwashed with sat. NaHCO3 solution (2×3 mL)
customThe solvents were removed by evaporation under reduced pressure

Sources & evidence

ORD record: ord-68d546a2063d4c7aac7ce93ac4a565f2
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618282B2

Reaction notes

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