Thionyl Chloride → HCID 66789154, compound

HRID 641271Notes

Reaction equation

HRID 641271 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:34][CH3:35])=[C:6]([S:8]([N:11]2[C:16]3[CH:17]=[C:18]([C:21]([NH:23][C:24]4[CH:32]=[CH:31][C:27]([C:28]([OH:30])=[O:29])=[CH:26][C:25]=4[CH3:33])=[O:22])[CH:19]=[CH:20][C:15]=3[O:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=1.S(Cl)(Cl)=O.[CH3:40]OC(=O)C1C=CC(N)=C(C)C=1>C1(C)C=CC=CC=1.CN(C)C=O>[CH3:40][O:29][C:28](=[O:30])[C:27]1[CH:31]=[CH:32][C:24]([NH:23][C:21]([C:18]2[CH:19]=[CH:20][C:15]3[O:14][CH2:13][CH2:12][N:11]([S:8]([C:6]4[CH:7]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=4[O:34][CH3:35])(=[O:10])=[O:9])[C:16]=3[CH:17]=2)=[O:22])=[C:25]([CH3:33])[CH:26]=1

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 2736799Methyl 4-amino-3-methylbenzoateHCID 24762474HCID 24762474, compound

Product 1

HCID 66789154HCID 66789154, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Procedure

4-{[4-(5-Chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-3-methyl-benzoic acid, MS (ISP): m/e=515.3 (M−H), was prepared as described in example 1, steps 1 to 6. Step 5 was performed using thionyl chloride in toluene and dimethyl-formamide for the formation of the acyl chloride, and 4-amino-3-methyl-benzoic acid methyl ester was used for the coupling, yielding 4-{[4-(5-chloro-2-methoxy-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazine-6-carbonyl]-amino}-3-methyl-benzoic acid methyl ester, which was hydrolyzed in step 6.

Sources & evidence

ORD record
ord-cbc0b57db0bf427d90dbd0eae60d816d
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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