Chlorosulfonic acid → 6-Acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride

HRID 2104262

Reaction equation

HRID 2104262 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[CH3:6][O:7][C:8]1[CH:17]=[C:16]2[C:11]([CH2:12][CH2:13][CH:14]([NH:18][C:19](=[O:21])[CH3:20])[CH2:15]2)=[CH:10][CH:9]=1>>[C:19]([NH:18][CH:14]1[CH2:13][CH2:12][C:11]2[CH:10]=[C:9]([S:2]([Cl:1])(=[O:5])=[O:3])[C:8]([O:7][CH3:6])=[CH:17][C:16]=2[CH2:15]1)(=[O:21])[CH3:20]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 100136977-Methoxy-2-acetamido-tetralin

Product 1

HCID 866013156-Acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride

Conditions

Temperature
-10 °C

Procedure

To chlorosulfonic acid (15 mL), cooled to −10° C. was added N-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-acetamide (1.44 g; 6.6 mmol). The reaction mixture was stirred at −10° C. for 15 min and quenched carefully by pouring over ice-water. The aqueous phase was extracted with CH2Cl2 (3×), the organic extracts combined, dried over Na2SO4, filtered and evaporated under reduced pressure to yield 6-acetylamino-3-methoxy-5,6,7,8-tetrahydronaphthalene-2-sulfonyl chloride as a white solid.

Workup

  1. customquenched carefully
  2. additionby pouring over ice-water
  3. extractionThe aqueous phase was extracted with CH2Cl2 (3×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-98e8c080765c4f459cc7d30a76be4397
Source dataset
uspto-grants-2009_08
Patent number
US07576238B2

Linked notes

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