3-Formylphenyl acetate → HCID 86583860, compound

HRID 412983Notes

Reaction equation

HRID 412983 reaction equation
O[C:2]1[CH:3]=[C:4]([CH2:8][CH:9]([NH:11][C:12]2[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=2[CH3:17])C)C=[CH:6][CH:7]=1.NC1C=C(C([O:31]C)=S)SC=1C.C(OC1C=C(C=CC=1)C=O)(=O)C>>[OH:31][C:3]1[CH:4]=[C:8]([CH2:9][NH:11][C:12]2[CH:13]=[C:14]([C:18]([O:20][CH3:21])=[S:19])[S:15][C:16]=2[CH3:17])[CH:6]=[CH:7][CH:2]=1

Participants

4

Reactant 3

HCID 1186183-Formylphenyl acetateHCID 86583856Methyl 4-amino-5-methylthiothiophene-2-carboxylateHCID 86758978HCID 86758978, compound

Product 1

HCID 86583860HCID 86583860, compound

Procedure

Methyl 4-{[(3-hydroxyphenyl)methylethyl]amino}-5-methylthiothiophene-2-carboxylate: Using the procedure described in Example 220, step (a), 61.6 mg (0.30 mmol) of methyl 4-amino-5-methylthiothiophene-2-carboxylate, 49.5 mg (0.30 mmol) of 3-acetoxybenzaldehyde, and 135 mg (2.2 equiv, 0.63 mmol) of NaHB(OAc)3 were allowed to react to give methyl 4-{[(3-hydroxyphenyl)methyl]amino}-5-methylthiothiophene-2-carboxylate. Mass spectrum (ESI, m/z): Calcd. for C14H16NO3S2, 352.07 (M+H), found, 350.2 (imine), 352.1.

Workup

  1. customto react

Sources & evidence

ORD record
ord-5abf93a04cdc4910b92ba8b9be88a8eb
Source dataset
uspto-grants-2003_05
Patent number
US06562840B1

Reaction notes

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