Formaldehyde → 3-{[Bis(2-ethylhexyl)amino]methyl}-1,3-benzothiazole-2(3H)-thione

HRID 648865Notes

Reaction equation

[SH:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[CH2:11]=O.[CH2:13]([CH:15]([CH2:26][CH2:27][CH2:28][CH3:29])[CH2:16][NH:17][CH2:18][CH:19]([CH2:24][CH3:25])[CH2:20][CH2:21][CH2:22][CH3:23])[CH3:14]>CO>[CH2:24]([CH:19]([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:18][N:17]([CH2:11][N:6]1[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3][C:2]1=[S:1])[CH2:16][CH:15]([CH2:13][CH3:14])[CH2:26][CH2:27][CH2:28][CH3:29])[CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 250.8 g (1.5 moles) of 2-mercaptobenzothiazole in 1500 ml of methanol are added 112.8 ml (1.5 moles) of 37% aqueous formaldehyde, followed by the dropwise addition, with stirring, of 362.4 g (1.5 moles) of bis(2-ethylhexyl)amine. The mixture is stirred for 15 hours at 50° C. and then concentrated by evaporation in vacuo, affording as residue 618 g of 3-[bis(2-ethylhexyl)aminomethyl]benzothiazoline-2-thione as a reddish brown oil

Workup

additionfollowed by the dropwise addition
concentrationconcentrated by evaporation in vacuo

Sources & evidence

ORD record: ord-6a557dd9706e4bf68f4df67c23bdcbb4
Source dataset: uspto-grants-1988_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04737302

Reaction notes

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