HCID 14809494, compound → HCID 20143011, compound

HRID 649331Notes

Reaction equation

HRID 649331 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1([S:22][CH3:23])[C:15](=[O:16])[N:14]([CH3:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]1.[CH2:24]([CH:26]([CH2:30]C)[C:27]([OH:29])=[O:28])[CH3:25].[Cl:32][CH2:33][CH2:34][CH:35]=O.Cl.[CH3:38][NH:39][CH2:40][CH:41]([C:43]1[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[C:45]([O:51][CH3:52])[CH:44]=1)[CH3:42]>>[CH2:40]([O:29][CH:27]([O:28][CH2:34][CH3:35])[CH2:26][CH2:30][O:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1([S:22][CH3:23])[C:15](=[O:16])[N:14]([CH3:17])[C:13]2[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=2[S:11]1)[CH3:41].[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:44][CH2:45][CH:46]=[O:49])=[C:3]([C:10]2([S:22][CH3:23])[C:15](=[O:16])[N:14]([CH3:17])[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=3[S:11]2)[CH:4]=1.[ClH:32].[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([O:1][CH2:24][CH2:25][CH2:38][N:39]([CH2:40][CH:41]([C:43]2[CH:48]=[CH:47][C:46]([O:49][CH3:50])=[C:45]([O:51][CH3:52])[CH:44]=2)[CH3:42])[CH3:33])=[C:3]([C:10]2([S:22][CH3:23])[C:15](=[O:16])[N:14]([CH3:17])[C:13]3[CH:18]=[CH:19][CH:20]=[CH:21][C:12]=3[S:11]2)[CH:4]=1

Participants

6

Reactant 3

HCID 14809494HCID 14809494, compoundHCID 20143023HCID 20143023, compoundHCID 86742111HCID 86742111, compound

Product 3

HCID 20143011HCID 20143011, compoundYield 72%HCID 20143097HCID 20143097, compoundYield 12.8%HCID 20143168HCID 20143168, compoundYield 64.9%

Procedure

3,4-Dihydro-2-(2-hydroxy-5-methoxyphenyl)-4-methyl-2-methylthio-3-oxo-2H-1,4-benzothiazine (5.2 g, compound No. 8), β-chloropropionaldehyde diethyl acetate (3.0 g) and N-methyl-2-(3,4-dimethoxyphenyl)propylamine hydrochloride (5.2 g) are treated by the similar method as in Example 26 to give 4.7 g (64.9%) of 2-[2-(3,3-diethoxypropoxy)-5-methoxyphenyl]-3,4-dihydro-4-methyl-2-methylthio-3-oxo-2H-1,4-benzothiazine (compound No. 21, (IR: neat, cm-1) 1660, 1555, 1048, 750), 2.8 g (72.0%) of 3,4-dihydro-2-[5-methoxy-2-(3-oxopropoxy)phenyl]-4-methyl-2-methylthio-3-oxo-2H-1,4-benzothiazine (compound No. 22, (IR: neat, cm-1) 1722, 1658, 1588, 1036, 748) and 0.6 g (12.8%) of the titled compound (mp. 153°-156.5° C. (dec.)).

Sources & evidence

ORD record
ord-29f48d8f315246dc918b6e4e7ecb102d
Source dataset
uspto-grants-1988_04
Patent number
US04739050

Reaction notes

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