Iodine chloride → HCID 12761852, compound

HRID 236918Notes

Reaction equation

HRID 236918 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH2:12][NH:13][S:14]([OH:17])(=[O:16])=[O:15].[I:18]Cl>O.O1CCCC1.Cl>[OH:1][C:2]1[C:7]([I:18])=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[CH2:12][NH:13][S:14]([OH:17])(=[O:16])=[O:15]

Participants

5

Reactant 2

HCID 24640Iodine chlorideHCID 12761851HCID 12761851, compound

Product 1

HCID 12761852HCID 12761852, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
20 °C

Procedure

To a solution of 2-hydroxy-5-(1,1-dimethylethyl)phenylmethanesulfamic acid (2.6 g., 0.01 mole) in water-tetrahydrofuran (5:1; v:v; 90 ml.) is added a freshly prepared solution of iodine monochloride (1.64 g., 0.01 mole) in 3 N hydrochloric acid (12 ml.) portionwise over 5 minutes providing a dark reaction solution which is stirred at 20° C. for 2 hours and then cooled to 0°-5° C. The resulting insoluble solid is collected, washed with 12 N hydrochloric acid, dried with aspiration at 20° C. and washed with water to give crude 2-hydroxy-3-iodo-5-(1,1-dimethylethyl)phenylmethanesulfamic acid (3.3 g., 85.9%), m.p. 172°-180° C. with dec. Recrystallization from water-ethanol (10:1; v:v) provides pure 2-hydroxy-3-iodo-5-(1,1-dimethylethyl)phenylmethanesulfamic acid as colorless crystals, m.p. 180°-182° C. with dec.

Workup

  1. customproviding a dark reaction solution which
  2. temperaturecooled to 0°-5° C
  3. customThe resulting insoluble solid is collected
  4. washwashed with 12 N hydrochloric acid
  5. customdried with aspiration at 20° C.
  6. washwashed with water
  7. customto give crude 2-hydroxy-3-iodo-5-(1,1-dimethylethyl)phenylmethanesulfamic acid (3.3 g., 85.9%), m.p. 172°-180° C. with dec
  8. customRecrystallization from water-ethanol (10:1; v:v)

Sources & evidence

ORD record
ord-e6c06ef198264ee4bc35b47c216ffb9a
Source dataset
uspto-grants-1979_06
Patent number
US04159279

Reaction notes

Loading…