Methanesulfonyl chloride → HCID 10384564, compound

HRID 1684111Notes

Reaction equation

HRID 1684111 reaction equation
O[CH2:2][C:3]1[N:4]([CH3:24])[C:5](=[O:23])[C:6]2[C:7]([N:22]=1)=[C:8]([OH:21])[C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12]([CH2:17]O)=[N:13][C:14]=1[C:15]=2[OH:16].[Li+].[Cl-:26].CS([Cl:31])(=O)=O.[K+].[Br-]>CN(C)C=O.O>[Cl:26][CH2:2][C:3]1[N:4]([CH3:24])[C:5](=[O:23])[C:6]2[C:7]([N:22]=1)=[C:8]([OH:21])[C:9]1[C:10](=[O:20])[N:11]([CH3:19])[C:12]([CH2:17][Cl:31])=[N:13][C:14]=1[C:15]=2[OH:16]

Participants

7

Reactant 4

HCID 31297Methanesulfonyl chlorideHCID 253877Potassium BromideHCID 433294Lithium ChlorideHCID 10065450HCID 10065450, compound

Product 1

HCID 10384564HCID 10384564, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 105 mg (0.313 mmol) of 20 in 10 mL of dry dimethyl formamide, were added 66 mg (1.56 mmol) of LiCl and 191 mg (1.56 mmol) of dimethylaminopyrldine. To this mixture was added 120 μL (1.56 mmol ) of methanesulfonyl chloride and the resulting solution gently heated with a heat gun until it became homogenous. After stirring this mixture at room temperature for 6 h, it was combined with 100 mL of water and the resulting mixture allowed to stir for an additional 2 hours. The resulting yellow precipitate was filtered, rinsed with water, and dried: 99 mg (85%) yield; mp >275° C. dec; IR (KBr pellet) 3036, 1645, 1603, 1421, 1372, 1343, 1270, 1240, 1015, 794 cm-1 ; 1H NMR (dimethyl-d6 sulfoxide) δ11.84 (2H, s, 5- and 10-hydroxyl) 4.95 (4H, s, methylenes), 3.65 (6H, s, 3- and 8- methyls); mass spectrum (EI, solids probe), m/z 370 (P+, 35Cl35Cl), 372 (P+, 37Cl35Cl), 374 (P+, 37Cl37Cl). Anal. Calcd for C14H12Cl2N4O4 : C, 45.30, H, 3.26; N, 15.09. Found: C, 45.76; H, 3.47; N, 13.99.

Workup

  1. temperaturethe resulting solution gently heated with a heat gun until it
  2. stirringto stir for an additional 2 hours
  3. filtrationThe resulting yellow precipitate was filtered
  4. washrinsed with water
  5. customdried
  6. custom99 mg (85%) yield

Sources & evidence

ORD record
ord-7120167571c24e5cb9acd65674ed5fd1
Source dataset
uspto-grants-1997_06
Patent number
US05639881

Reaction notes

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