Chloroacetyl chloride → 7-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

HRID 1712972Notes

Reaction equation

HRID 1712972 reaction equation
C([O-])([O-])=O.[K+].[K+].Cl.[NH2:8][C:9]1[CH:15]=[CH:14][C:12]([OH:13])=[CH:11][C:10]=1[OH:16].Cl[CH2:18][C:19](Cl)=[O:20]>O.C1(C)C=CC=CC=1>[OH:13][C:12]1[CH:14]=[CH:15][C:9]2[NH:8][C:19](=[O:20])[CH2:18][O:16][C:10]=2[CH:11]=1

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 100578707-hydroxy-3,4-dihydro-2H-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
2.5 °C

Procedure

K2CO3 (250 g, 1.8 mol, 4 eq) was dissolved in water (1100 mL) in a 3 L round bottomed flask, vacuum degassed 3 times, then cooled to 0 to 5° C. 4-Amino resorcinol HCl (73 g, 0.45 mol, 1 eq) was added though a strong nitrogen purge, and the blue solution was again degassed 3×. Choroacetyl chloride (45 mL, 64 g, 0.57 mol, 1.25 eq) was dissolved in toluene (225 mL), and was added over 1 h maintaining the temperature below 5° C. the ice bath was removed, and the mixture (biphasic with suspended crystalline product) was stirred overnight. The intermediate 2 was then isolated via filtration giving 53 g (71%) after a water wash (550 mL) and drying.

Workup

  1. customvacuum degassed 3 times
  2. custompurge
  3. customthe blue solution was again degassed 3×
  4. additionwas added over 1 h
  5. customwas removed

Sources & evidence

ORD record
ord-f9d40adae2164830a470322a546d9f2a
Source dataset
uspto-grants-2010_09
Patent number
US07795254B2

Reaction notes

Loading…