Acetic Anhydride → HCID 21997631, compound

HRID 1977106Notes

Reaction equation

HRID 1977106 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[S:12][CH2:13][C:14]#[N:15].[C:16](OC(=O)C)(=[O:18])[CH3:17]>>[C:14]([CH2:13][S:12][C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[NH:1][C:16](=[O:18])[CH3:17])#[N:15]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 21997632HCID 21997632, compound

Product 1

HCID 21997631HCID 21997631, compound

Procedure

(2-Amino-4-trifluoromethylphenylsulfanyl)acetonitrile (0.66 g) was stirred on an ice bath at 0° C. Acetic acid anhydride (2.5 ml) was added, and the resulting solution was allowed to reach room temperature. After 1 h the mixture was concentrated in vacuo and the solid residue was triturated with petroleum ether (2×2 ml), filtered off and and dried to give the title compound as a white solid. Yield 0.75 g (96%), mp 103-103.3° C.; 1H-NMR(CDCl3) δ (ppm): 8.79 (br, 1H), 8.36 (br, 1H), 7.78 (d, 1H), 7.38 (dd, 1H, J: 8 Hz/2 Hz), 3.50 (s, 2H) 2.29 (s, 3H); 13C-NMR (DMSO-d6) δ (ppm): 169.2 (C═O), 137.1, 134.3, 129.6, 127.7 (q, J=32 Hz), 122.7 (m, 2C), 123.9 (CF3, J=272), 117.6 (CN), 23.2 (H3), 17.6 (CH2); IR (KBr) ν (cm−1): 3249, 2244 (C≡N), 1660, 1530, 1483, 1335, 1170, 1116, 1095.

Workup

  1. customto reach room temperature
  2. concentrationAfter 1 h the mixture was concentrated in vacuo
  3. customthe solid residue was triturated with petroleum ether (2×2 ml)
  4. filtrationfiltered off
  5. customdried

Sources & evidence

ORD record
ord-669cad6f47c44444b1d1ff503962a8a8
Source dataset
uspto-grants-2001_05
Patent number
US06232310B1

Reaction notes

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