Acrylamide → HCID 12952187, compound

HRID 905137Notes

Reaction equation

HRID 905137 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.C(N(CC)CC)C.[C:18]([NH2:22])(=[O:21])[CH:19]=[CH2:20]>O>[S:1]=[C:2]1[N:6]([CH2:20][CH2:19][C:18]([NH2:22])=[O:21])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1

Participants

5

Reactant 3

HCID 6579AcrylamideHCID 8471TriethylamineHCID 178418395HCID 178418395, compound

Product 1

HCID 12952187HCID 12952187, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution at 50° C. containing 86 g (0.5 mol) of 2-mercaptobenzothiazole, 60.8 g (0.6 mol) of triethylamine and 500 ml of water, 43 g (0.6 mol) of acrylamide was added in one portion. After stirring at 60°-70° C. for 24 hours, the stirred reaction mixture was cooled to 25° C., the solid collected by filtration, washed with water until neutral and airdried at 50° C. The product, 2-thioxo-3(2H)-benzothiazole-propanamide, mp 226°-227° C. was obtained in 77% yield.

Workup

  1. additionwas added in one portion
  2. customthe stirred reaction mixture
  3. filtrationthe solid collected by filtration
  4. washwashed with water until neutral and airdried at 50° C

Sources & evidence

ORD record
ord-4ea8a0f1468e4dbdbb541b27dac8005a
Source dataset
uspto-grants-1983_12
Patent number
US04422865

Reaction notes

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