Chlorosulfonic acid → 3-Bromo-5-{[2-(morpholin-4-yl)ethyl]carbamoyl}thiophene-2-sulfonyl Chloride

HRID 516808Notes

Reaction equation

HRID 516808 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:7]([NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[O:8])[S:5][CH:6]=1.[Cl:18][S:19](O)(=[O:21])=[O:20]>>[Br:1][C:2]1[CH:3]=[C:4]([C:7](=[O:8])[NH:9][CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[S:5][C:6]=1[S:19]([Cl:18])(=[O:21])=[O:20]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 230637244-Bromo-N-(2-morpholin-4-ylethyl)thiophene-2-carboxamide

Product 1

HCID 866319333-Bromo-5-{[2-(morpholin-4-yl)ethyl]carbamoyl}thiophene-2-sulfonyl Chloride

Conditions

Temperature
95 °C

Procedure

To a flask containing 4-bromo-N-[2-(morpholin-4-yl)ethyl]thiophene-2-carboxamide (1.6 g, 5.1 mmol) was added chlorosulfonic acid (10 ml, 30 equiv). The reaction was heated to 95° C. for 90 minutes before careful addition to ice. The resulting solid was filtered and dried in vacuo. The crude material was trituated with heptane:ethyl acetate to afford the title compound without need for further purification (0.62 g, 29%). δH (500 MHz, DMSO-d6) 9.01 (1H, t, 5.5 Hz), 7.76 (1H, s), 3.97 (2H, d, 10.4 Hz), 3.78 (2H, t, 11.5 Hz), 3.63 (2H, q, 6.0 Hz), 3.51 (2H, d, 12.3 Hz), 3.29 (2H, q, 5.7 Hz), 3.03-3.17 (2H, m), TR=1.22 min.

Workup

  1. filtrationThe resulting solid was filtered
  2. customdried in vacuo

Sources & evidence

ORD record
ord-01cca6701d7f4b449ef58cfeb346fd71
Source dataset
uspto-grants-2015_08
Patent number
US09115064B2

Reaction notes

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