Hydrochloric Acid → Isopropyl 2-(aminosulfonyl)-4-chlorobenzoate

HRID 1285274Notes

Reaction equation

HRID 1285274 reaction equation
Cl.[Cl:2][C:3]1[CH:14]=[CH:13][C:6]2[C:7](=[O:12])[NH:8][S:9](=[O:11])(=[O:10])[C:5]=2[CH:4]=1.[CH3:15][CH:16]([OH:18])[CH3:17]>>[CH3:15][CH:16]([O:18][C:7](=[O:12])[C:6]1[CH:13]=[CH:14][C:3]([Cl:2])=[CH:4][C:5]=1[S:9]([NH2:8])(=[O:11])=[O:10])[CH3:17]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 1008076-Chlorosaccharin

Product 1

HCID 13564712Isopropyl 2-(aminosulfonyl)-4-chlorobenzoate

Conditions

Temperature
80 °C

Procedure

Anhydrous hydrogen chloride was passed into a mixture of 773.7 g of 6-chloro-1,2-benzothiazole-3-one-1,1-dioxide and 7 L of 2-propanol until the mixture was saturated (7.5 hr.). The mixture was heated at reflux (80° C.) for 1.5 hr., then cooled to 0° C. The precipitated solids were collected and dried to give 893.9 g of the title compound, m.p. 143°-145° C. A second crop (44.5 g, m.p. 140°-142° C.) and third crop (125 g, m.p. 133°-135° C.) were obtained by concentrating the mother liquors in vacuo.

Workup

  1. custom(7.5 hr.)
  2. temperatureThe mixture was heated
  3. temperature, then cooled to 0° C
  4. customThe precipitated solids were collected
  5. customdried

Sources & evidence

ORD record
ord-4c046ce1e9134d36b4c175bd4dba1c19
Source dataset
uspto-grants-1986_01
Patent number
US04566898

Reaction notes

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