Acetic Acid → HCID 22007157, compound

HRID 323789Notes

Reaction equation

HRID 323789 reaction equation
[Cl:1][CH2:2][CH:3]([C:5]1[CH:10]=[C:9]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:8]=[CH:7][C:6]=1[O:15][CH3:16])[OH:4].ClCCl.C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C.[C:44](O)(=[O:46])[CH3:45]>CN(C)C=O>[C:44]([O:4][CH:3]([CH2:2][Cl:1])[C:5]1[CH:10]=[C:9]([S:11](=[O:14])(=[O:13])[NH2:12])[CH:8]=[CH:7][C:6]=1[O:15][CH3:16])(=[O:46])[CH3:45]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 22007170HCID 22007170, compound

Product 1

HCID 22007157HCID 22007157, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.64 g (9.9 mmol) of α-chloromethyl-2-methoxy-5-sulphamoylbenzenemethanol and 100 ml of dichloromethane are introduced into a 250-ml round-bottomed flask. 10 ml of dimethylformamide are then added with stirring, followed by 852 μl of acetic acid, 2.56 g of dicyclohexylcarbodiimide and 121 mg of dimethylaminopyridine. The mixture is allowed to react for 1 hour at room temperature, and is then filtered and rinsed with 50 ml of 5% sodium hydrogen carbonate solution and then with 50 ml of water. The rinsing liquors are extracted with 2 times 20 ml of acetic acid, and the organic phases are then combined, dried and concentrated. On chromatographing the residue on a silica column with a 25:75 mixture of ethyl acetate and cyclohexane, 1.9 g of product are obtained.

Workup

  1. customto react for 1 hour at room temperature
  2. filtrationis then filtered
  3. washrinsed with 50 ml of 5% sodium hydrogen carbonate solution
  4. extractionThe rinsing liquors are extracted with 2 times 20 ml of acetic acid
  5. customdried
  6. concentrationconcentrated
  7. additionOn chromatographing the residue on a silica column with a 25:75 mixture of ethyl acetate and cyclohexane, 1.9 g of product
  8. customare obtained

Sources & evidence

ORD record
ord-d0a89714aabb4aeda531bde5490cc495
Source dataset
uspto-grants-2001_04
Patent number
US06214882B1

Reaction notes

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