Chlorosulfonic acid → HCID 57891991, compound

HRID 1820851Notes

Reaction equation

HRID 1820851 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[F:6][C:7]([F:21])([F:20])[C:8]([NH:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:9]>>[F:6][C:7]([F:20])([F:21])[C:8]([NH:10][CH:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:2]([Cl:1])(=[O:5])=[O:3])[CH:17]=2)[CH2:12]1)=[O:9]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 10307996N-(2,3-dihydro-1H-inden-2-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 57891991HCID 57891991, compoundYield 71%

Procedure

After cooling chlorosulfonic acid (3.0 ml) to −78° C. under nitrogen, 2,2,2-trifluoro-N-(2,3-dihydro-1H-inden-2-yl)acetamide (500.0 mg, 2.2 mmol) was added and then allowed to warm up to rt. The solution was poured into an ice-water mixture (100.0 ml), followed by an extraction with EtOAc. The organic layer was dried over MgSO4 and evaporated in vacuo. The residue was triturated with Et2O to obtain the product as a white solid (510.0 mg, 71% yield). 1H-NMR (400 MHz, DMSO-d6) δ 7.93-7.91 (m, 2H), 7.51-7.49 (m, 1H), 6.50 (s, 1H), 4.91-4.83 (m, 1H), 3.52 (dd, J=16.8, 7.3 Hz, 2H), 3.05 (dd, J=17.0, 4.8 Hz, 2H).

Workup

  1. extractionfollowed by an extraction with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. customevaporated in vacuo
  4. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-252f357d8bb14a6db8399776a34f479c
Source dataset
uspto-grants-2009_10
Patent number
US07605174B2

Reaction notes

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