Formaldehyde → 3-(Anilinomethyl)-1,3-benzothiazole-2(3H)-thione

HRID 1381480Notes

Reaction equation

HRID 1381480 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:8][C:9]1[S:10][C:11]2[CH:17]=[CH:16][CH:15]=[CH:14][C:12]=2[N:13]=1.[CH2:18]=O>C(O)C>[C:2]1([NH:1][CH2:18][N:13]2[C:12]3[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=3[S:10][C:9]2=[S:8])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6115AnilineHCID 178418395HCID 178418395, compound

Product 1

HCID 2204713-(Anilinomethyl)-1,3-benzothiazole-2(3H)-thioneYield 86.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With stirring, 18.63 g (0.2 mole) of aniline are added to a suspension of 33.45 g (0.2 mole) of 2-mercaptobenzothiazole in 120 ml of ethanol, the temperature rising to 30° C. Then 16.4 g (0.2 mole) of 37% aqueous formaldehyde solution are added and stirring is continued for 30 minutes. The precipitate is isolated by filtration and washed with cold ethanol and hexane, affording 47 g of 3-(phenylaminomethyl)benzothiazoline-2-thione which melts at 102°-103° C.

Workup

  1. customrising to 30° C
  2. stirringstirring
  3. customThe precipitate is isolated by filtration
  4. washwashed with cold ethanol and hexane

Sources & evidence

ORD record
ord-68e2e0f028134758833a90ba2e7afc2b
Source dataset
uspto-grants-1989_02
Patent number
US04803001

Reaction notes

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