Sulfuryl chloride → HCID 13180269, compound

HRID 1074419Notes

Reaction equation

HRID 1074419 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[S:13]([N:16]([CH3:18])[CH3:17])(=[O:15])=[O:14])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][CH:4]=1.S(Cl)([Cl:25])(=O)=O>C(O)(=O)C>[Cl:25][C:4]1[CH:5]=[C:6]([C:19]([OH:21])=[O:20])[C:7]2[C:12]([C:3]=1[O:2][CH3:1])=[C:11]([S:13]([N:16]([CH3:17])[CH3:18])(=[O:15])=[O:14])[CH:10]=[CH:9][CH:8]=2

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 131802685-(Dimethylsulfamoyl)-4-methoxynaphthalene-1-carboxylic acid

Product 1

HCID 13180269HCID 13180269, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Methoxy-5-(dimethylaminosulfonyl)-1-naphthalenecarboxylic acid (15.26 g, 50 mmoles), described in Example 1a) was suspended in acetic acid (46 ml). Sulfuryl chloride (6 ml, 75 mmoles) was added portionwise to the suspension at such a rate that the temperature did not exceed 32° C. The resulting solution was stirred at 20°-22° C. for 2 hr and then poured into 460 ml of ice water. The mixture was stirred for 30 min. The precipitate was collected and dried over P2O5 to give 16.7 g of the title compound; mp 127°-137° C.; NMR (CDCl3) δ 3.05 (s, 6H), 4.12 (s, 3H), 8.0 (broad, 1H), 7.7 and 9.25 (m, 4H).

Workup

  1. customdid not exceed 32° C
  2. stirringThe mixture was stirred for 30 min
  3. customThe precipitate was collected
  4. dry with materialdried over P2O5

Sources & evidence

ORD record
ord-1889e770b4014c47987f616c522f12aa
Source dataset
uspto-grants-1983_07
Patent number
US04391816

Reaction notes

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