1,2-Dichloroethane → HCID 10007831, compound

HRID 269542Notes

Reaction equation

HRID 269542 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]1[C:17]([C:22]2[C:23]([C:28](O)=[O:29])=[CH:24][CH:25]=[CH:26][CH:27]=2)=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:31]1([S:37]([NH2:40])(=[O:39])=[O:38])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(Cl)CCl.ClCCl.O1CCCC1>CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[C:16]1[C:17]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[C:28]([NH:40][S:37]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:39])=[O:38])=[O:29])=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7370BenzenesulfonamideHCID 21919333Tetrahydrofurane dichloromethaneHCID 44581620HCID 44581620, compound

Product 1

HCID 10007831HCID 10007831, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyloxy-5-chloro-[1,1′;2′,1″]terphenyl-2″-carboxylic acid (100 mg, 0.24 mmol), benzenesulphonamide (46 mg, 0.29 mmol), EDC (56 mg, 0.29 mmol), and 4-dimethylaminopyridine (5 mg, 0.03 mmol) in 1:1 dichloromethane/tetrahydrofuran (4 ml) was stirred at room temperature for 16 hours. The mixture was diluted with ethyl acetate (10 ml) and washed with aq. sodium bicarbonate (5 ml), dilute hydrochloric acid (5 ml), water (5 ml), and brine (5 ml). The organic phase was dried and evaporated. Purification by prep. HPLC gave the title compound. (27 mg 20%).

Workup

  1. washwashed with aq. sodium bicarbonate (5 ml), dilute hydrochloric acid (5 ml), water (5 ml), and brine (5 ml)
  2. customThe organic phase was dried
  3. customevaporated
  4. customPurification by prep

Sources & evidence

ORD record
ord-16cb7d8ff9d54875b649e03104922f7b
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

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