Chlorosulfonic acid → (+/-)-2-Carbamoylchroman-6-sulfonyl chloride

HRID 1071162Notes

Reaction equation

HRID 1071162 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH:2]1[C:11]([NH2:13])=[O:12].[Cl:14][S:15](O)(=[O:17])=[O:16]>>[C:11]([CH:2]1[CH2:3][CH2:4][C:5]2[C:10](=[CH:9][CH:8]=[C:7]([S:15]([Cl:14])(=[O:17])=[O:16])[CH:6]=2)[O:1]1)(=[O:12])[NH2:13]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 18621312Chroman-2-carboxamide

Product 1

HCID 22471744(+/-)-2-Carbamoylchroman-6-sulfonyl chlorideYield 73%

Procedure

The compound from Example 21 (2.0 g, 11.3 mmol) was added in portions over 10 minutes to cooled (0° C.) chlorosulfonic acid (9 mL). After 75 minutes the mixture was added slowly and dropwise to ice (150 g). The mixture was filtered and the solids washed with water (3×20 mL) and dried at 50° C. in vacuo to give a colorless powder (2.29 g, 73%). Mp 147-148° C.; 1H NMR (CDCl3, 300 MHz) δ 7.82 (m, 2H), 7.08 (d, J=8.6 Hz, 1H), 6.50 (br s, 1H), 5.77 (br s, 1H), 4.68 (dd, J=9.4 Hz, 3.1 Hz, 1H), 2.95 (m, 2H), 2.52 (m, 1H), 2.16 (m, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe solids washed with water (3×20 mL)
  3. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-2081c1e1fd8e4f1f8286a240003b2f43
Source dataset
uspto-grants-2005_06
Patent number
US06903218B2

Reaction notes

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