Formamide → HCID 17990151, compound

HRID 1292969Notes

Reaction equation

HRID 1292969 reaction equation
[CH:1]([NH2:3])=O.[NH2:4][C:5]1[S:6][C:7]2[CH2:22][C:17]3([O:21][CH2:20][CH2:19][O:18]3)[CH2:16][CH2:15][C:8]=2[C:9]=1[C:10](OCC)=[O:11].C([O-])=O.[NH4+]>>[O:18]1[CH2:19][CH2:20][O:21][C:17]21[CH2:16][CH2:15][C:8]1[C:9]3[C:10](=[O:11])[NH:3][CH:1]=[N:4][C:5]=3[S:6][C:7]=1[CH2:22]2

Participants

4

Reactant 3

HCID 713FormamideHCID 2723923Ammonium formateHCID 10902110Ethyl 2-amino-4,7-dihydro-5H-spiro[1-benzothiophere-6,2'-[1,3]dioxolane]-3-carboxylate

Product 1

HCID 17990151HCID 17990151, compoundYield 88%

Conditions

Temperature
140 °C

Procedure

To a stirring 225 mL formamide solution of ethyl 2-amino-4,7-dihydro-5H-spiro[1-benzothiophene-6,2′-[1,3]dioxolane]-3-carboxylate (40.0 g, 0.142 mol) was added ammonium formate (17.8 g, 0.282 mol). The contents were stirred with heating at 140° C. for 16 h, after which time the heterogeneous contents were removed from heating, and allowed to cool to rt. The contents were filtered, the solid filter cake washed with water (2×60 mL), and suction dried overnight to afford the desired product as an off-white solid (33.0 g, 88%). 1H-NMR (DMSO-d6) δ 12.35 (broad s, 1H), 8.00 (s, 1H), 3.92 (s, 4H), 2.95 (t, 2H), 2.91 (s, 2H), 1.83 (t, 2H); LCMS RT=1.87 min; [M+H]+=265.2.

Workup

  1. customafter which time the heterogeneous contents were removed
  2. temperaturefrom heating
  3. temperatureto cool to rt
  4. filtrationThe contents were filtered
  5. filtrationthe solid filter cake
  6. washwashed with water (2×60 mL), and suction
  7. customdried overnight

Sources & evidence

ORD record
ord-732d866cf5fd486c8a857679e52e9c55
Source dataset
uspto-grants-2007_07
Patent number
US07238701B2

Reaction notes

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