Sulfamic Acid → HCID 55281029, compound

Temperature

0 °C

Title compound 9B, 5-amino-2-chloro-benzamide (1.05 g, 6.13 mmol) was dissolved in a concentrated aqueous solution of HCl (10 ml) and cooled to 0° C. To this a cooled solution of NaNO2 (0.54 g, 1.5 eq, 9.19 mmol) in water (4 ml) was added over 15 minutes whilst maintaining the temperature below 10° C. The reaction was then cooled to 0° C. and stirred for 1 hour. To the reaction mixture sulfamic acid (0.3 g, 0.5 eq, 3.06 mmol) was added portion wise over a 20 minute period, a solution of tin chloride dihydrate (4.15 g, 3.0 eq, 18.4 mmol) in a concentrated aqueous HCl solution (4 ml) was then added drop wise over a 20 minute period whilst maintaining the temperature below 15° C. The reaction mixture then stirred at 0° C. for 2 hours then basified to pH 14 with 5M NaOH (aq) whilst maintaining the reaction temperature below 30° C. The reaction mixture was then rapidly extracted with ethyl acetate (2×50 ml), the organics combined, washed with brine, dried over Na2SO4 and solvent removed in vacuo to give the title compound (0.33 g, 1.8 mmol, 29%). LC-MS: [M+H]+=186, Rt=0.53 min, 96% purity.

1. temperaturewhilst maintaining the temperature below 10° C
2. temperatureThe reaction was then cooled to 0° C.
3. temperaturewhilst maintaining the temperature below 15° C
4. stirringThe reaction mixture then stirred at 0° C. for 2 hours
5. temperaturewhilst maintaining the reaction temperature below 30° C
6. extractionThe reaction mixture was then rapidly extracted with ethyl acetate (2×50 ml)
7. washwashed with brine
8. dry with materialdried over Na2SO4 and solvent
9. customremoved in vacuo

ORD record

ord-a48f706ef16342ef845ba9b9ea8e7490

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08071607B2