Formaldehyde → 3-(Hydroxymethyl)-1,3-benzothiazol-2(3H)-one

HRID 2057351Notes

Reaction equation

HRID 2057351 reaction equation
[OH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:11][OH:12].C=O>O>[OH:12][CH2:11][N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]1=[O:1]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 887MethanolHCID 178517143HCID 178517143, compound

Product 1

HCID 27337513-(Hydroxymethyl)-1,3-benzothiazol-2(3H)-oneYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred slurry containing 30.2 g (0.2 mol) of 2-hydroxybenzothiazole and 40 ml of methyl alcohol, 32 ml of 37% aqueous formaldehyde was added in one portion. The stirred mixture was heated at 78°-80° C. (reflux) for 30 minutes. At 80° C., 60 ml of hot water was added to the stirred solution. After cooling to 0° C., the product was collected by filtration, washed with 100 ml of heptane and air-dried at 25°-30° C. The product, 3-(hydroxymethyl)-2-benzothiazolinone, mp. 101°-3° C., was obtained in 94% yield. After recrystallization from isopropyl alcohol the melting point remained unchanged.

Workup

  1. additionwas added in one portion
  2. temperatureThe stirred mixture was heated at 78°-80° C.
  3. temperature(reflux) for 30 minutes
  4. filtrationthe product was collected by filtration
  5. washwashed with 100 ml of heptane
  6. customair-dried at 25°-30° C

Sources & evidence

ORD record
ord-b725f7ce1c284a72ba7581eb1079676e
Source dataset
uspto-grants-1980_07
Patent number
US04210439

Reaction notes

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