Formaldehyde → 2-[(2,5-dioxo-1-pyrrolidinyl)methyl]amino-N-formyl-N-methyl-alpha-(3-methyl-2-thienyl)benzeneethanamine

HRID 486667Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[N:10]([CH:12]=[O:13])[CH3:11].[CH2:20]=O.[C:22]1(=[O:28])[NH:26][C:25](=[O:27])[CH2:24][CH2:23]1>C(O)C>[O:28]=[C:22]1[CH2:23][CH2:24][C:25](=[O:27])[N:26]1[CH2:20][NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH:9]([C:14]1[S:15][CH:16]=[CH:17][C:18]=1[CH3:19])[N:10]([CH:12]=[O:13])[CH3:11]

Participants

Conditions

Temperature: 98 °C

Procedure

A stirred solution of 8 g of 2-amino-N-formyl-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine in 30 ml of 95% ethanol was treated with 2.4 ml of a 37% formaldehyde solution and 3.6 g of succinimide. The solution was heated for 6 hours at 98° C. and then allowed to stand at ambient temperature for 24 hours. The resulting precipitate was filtered, washed (95% ethanol; 3×50 ml), and dried in vacuo (40° C.) to afford 7.62 g of 2-[(2,5-dioxo-1-pyrrolidinyl)methyl]amino-N-formyl-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, mp 160°-164° C.

Workup

filtrationThe resulting precipitate was filtered
washwashed (95% ethanol; 3×50 ml)
customdried in vacuo (40° C.)

Sources & evidence

ORD record: ord-a867537fb98d4b97ab6dc2bb5c5bcff7
Source dataset: uspto-grants-1994_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05292760

Reaction notes

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