Phosphorus sulfide (P2S5) → HCID 20605662, compound

HRID 481064Notes

Reaction equation

HRID 481064 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:9]2[C:10](=O)[NH:11][CH2:12][CH2:13][C:8]=2[N:7]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH:6]=1)=[O:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27]>N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:9]2[C:10](=[S:27])[NH:11][CH2:12][CH2:13][C:8]=2[N:7]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 20605661HCID 20605661, compound

Product 1

HCID 20605662HCID 20605662, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
65 °C

Procedure

In a round bottom flask under N2 atm. are the 1-[2-(4-Nitro-phenyl)-ethyl]-4-oxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridine-3-carboxylic acid methyl ester (48.64 mmol), P4S10 (24.32 mmol) and 240 mL pyridine combined and heated at 65° C. for 8 hours. After cooling to RT it is poured over ˜600 mL ice and stirred for 2 hours. The yellow solid is filtered off, washed (2×) with water and dried on the high vacuum for 18 h to yield 1-[2-(4-Nitro-phenyl)-ethyl]-4-thioxo-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-C]pyridine-3-carboxylic acid methyl ester, 10.24 g, as a yellow solid (65%): 1H NMR (CD3OD) 2.43 (t, 2H), 3.16 (t, 2H), 3.28-3.33 (m, 2H), 3.75 (s, 3H), 4.21 (t, 2H), 7.16 (s, 1H), 7.30 (d, 2H), 8.13 (d, 2H); LRMS calcd 359.41, found [M+H] 360.2.

Workup

  1. temperatureAfter cooling to RT it
  2. filtrationThe yellow solid is filtered off
  3. washwashed (2×) with water
  4. customdried on the high vacuum for 18 h

Sources & evidence

ORD record
ord-bc98b0879b6845949b82556e194d99be
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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