Methanesulfonyl chloride → HCID 59443764, compound

HRID 537235Notes

Reaction equation

HRID 537235 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:7]=[C:8]([CH:13]=[CH:14][C:15]=2[NH2:16])[C:9]([O:11][CH3:12])=[O:10])[CH2:3][CH2:2]1.[CH3:17][S:18](Cl)(=[O:20])=[O:19]>N1C=CC=CC=1>[CH3:12][O:11][C:9](=[O:10])[C:8]1[CH:13]=[CH:14][C:15]([NH:16][S:18]([CH3:17])(=[O:20])=[O:19])=[C:6]([O:5][CH2:4][CH:1]2[CH2:3][CH2:2]2)[CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 43560608HCID 43560608, compound

Product 1

HCID 59443764HCID 59443764, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 3-(cyclopropylmethoxy)-4-aminobenzoate (8.86 g) was dissolved in pyridine (80 mL) at room temperature under N2 atmosphere. Methanesulfonyl chloride (4.04 mL) was added and the mixture was stirred at r.t. for 18 hours. The reaction mixture was evaporated to dryness, the crude was treated with 1N HCl (500 mL) and extracted with CH2Cl2 (3×200 mL). The organic layer was dried over Na2SO4 and the solvent was evaporated off to yield 11.7 g of the desired intermediate.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additionthe crude was treated with 1N HCl (500 mL)
  3. extractionextracted with CH2Cl2 (3×200 mL)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customthe solvent was evaporated off

Sources & evidence

ORD record
ord-fb1ddea00f7b41f187b7f5b6f5e94960
Source dataset
uspto-grants-2014_10
Patent number
US08859778B2

Reaction notes

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